ChemicalBook CAS DataBase List Benzamide, 2-amino-6-methoxy-

Benzamide, 2-amino-6-methoxy- synthesis

10synthesis methods

Product Name:Benzamide, 2-amino-6-methoxy-
CAS Number:1591-38-4
Molecular formula:C8H10N2O2
Molecular Weight:166.18

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Yield:1591-38-4 98%

Reaction Conditions:

Stage #1: 6-methoxyanthranilic acidwith benzotriazol-1-ol;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in tetrahydrofuran at 20; for 0.5 h;
Stage #2: with 4-methyl-morpholine;ammonium hydroxide in tetrahydrofuran;water at 20; for 18 h;

Steps:

57

To a solution of 2-amino-6-methoxybenzoic acid (9.0 g, 53.8 mmol) in THF (270 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (23.7 g, 123.7 mmol) and hydroxybenzotriazole (23.9 g, 156.0 mmol). The mixture was stirred at rt for 30 min, then N-methylmorpholine (18.2 g, 180.3 mmol) and NH₄OH ( 50 vol % in H₂O, 36 mL) were added. The reaction mixture was then stirred for 18 h at rt. After that time the reaction was concentrated under reduced pressure and diluted with ethyl acetate (600 mL). The organic phase was washed with brine (2×100 mL), dried over Na₂SO₄and concentrated under reduced pressure to give 2-amino-6-methoxybenzamide (8.80 g, 98%) as a light yellow solid: ¹H NMR (400 MHz, DMSO-d₆): δ 7.55 (br s, 1H), 7.29 (br s, 1H), 7.01 (t, J=8.4 Hz, 1H), 6.36 (br s, 2H), 6.30 (dd, J=8.4, 0.8 Hz, 1H), 6.17 (dd, J=8.0, 1.2 Hz, 1H), 3.76 (s, 3H)

References:

US2014/140956,2014,A1 Location in patent:Paragraph 0860

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References

38469-85-1
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References

5-methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

67765-42-8
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References

Carbamic acid, [2-(aminocarbonyl)-3-methoxyphenyl]-, 1,1-dimethylethyl ester (9CI)

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1591-38-4
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References