3-FLUORO-4-(N-MORPHOLINO)-BENZALDEHYDE synthesis
- Product Name:3-FLUORO-4-(N-MORPHOLINO)-BENZALDEHYDE
- CAS Number:495404-90-5
- Molecular formula:C11H12FNO2
- Molecular Weight:209.22
110-91-8
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34036-07-2
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495404-90-5
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Yield:495404-90-5 87 %
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at 130;
Steps:
2.1.2. General procedure for compounds 3a-d
General procedure: To the solution of 3,4-difluorobenzaldehyde (1 eq) in DMF, was added potassium carbonate (2 eq), followed by compound 2a-d (1.2 eq). The resultant suspension was heated at 130 °C for 16 h and then cooled to room temperature and poured into ice cold wa- ter. The precipitate was formed, filtered under suction and washed with ether and pentane to afford products 3a-b and 3d , while for compound 3c diluted with EtOAc and washed with cold brine so- lution. The organic layer was dried over anhydrous Na 2 SO 4 , fil- tered and concentrated under reduced pressure to get products 3a-d . 2.1.2.1. 3-fluoro-4-morpholinobenzaldehyde ( 3a ) Yellow solid, yield: 87%, mp: 63-66 °C; FTIR (ATR, V max , cm -1 ): 2977 (Ar- H str.), 1677 (C = O str.), 1606 (Ar C = C str.), 1238 (C -N str.), 1110 (C-F str.); 1 H NMR (600 MHz, DMSO-d 6 , 25 °C) δ 9.82 (s, 1H), 7.58 (d, J = 8.46 Hz, 1H), 7.52 (d, J = 13.50 Hz, 1H), 6.97 (t, J = 8.40 Hz, 1H), 3.86 (t, J = 5.12 Hz, 4H), 3.24 (t, J = 5.06 Hz, 4H). 13 C NMR (150 MHz, DMSO-d 6 , 25 °C) δ189.9, 155.7-154.0 (d, J C- F = 249 Hz, 1C), 145.3-145.2 (d, J C- F = 8.47 Hz, 1C), 130.55-130.51 (d, J C-F = 6.60 Hz, 1C), 128.0-127.9 (d, J C- F = 2.43 Hz, 1C), 117.79-117.77 (d, J C- F = 3.72 Hz, 1C), 116.3-116.1 (d, J C- F = 22.32 Hz, 1C), 66.8, 50.1.
References:
Kushwaha, Babita;Kushwaha, Narva Deshwar;Priya, Manisha;Chandrasekaran, Balakumar;Obakachi, Vincent A.;Chauhan, Ruchika;Kidwai, Saqib;Singh, Ramandeep;Ganai, Ab Majeed;Karpoormath, Rajshekhar [Journal of Molecular Structure,2023,vol. 1276,art. no. 134791]
495404-89-2
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495404-90-5
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369-25-5
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495404-90-5
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495405-04-4
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495404-90-5
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