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ChemicalBook CAS DataBase List 2-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-3-CARBOXYLIC ACID

2-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-3-CARBOXYLIC ACID synthesis

2synthesis methods
-

Yield:54329-54-3 53%

Reaction Conditions:

with hydrogenchloride;formaldehyd in formic acid;water;

Steps:

3 2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

PREPARATION 3 2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid A solution of 0.364 g (2.07 mmol) of 3-carboxy-1,2,3,4-tetrahydroisoquinoline in 25 mL of formic acid was combined with 2.5 mL of 37% formaldehyde. The resulting mixture was allowed to reflux for approximately 17 hours. After cooling, the mixture was contentrated under reduced pressure to provide a gum. This gum was dissolved in 3.0 mL of water, adjusted to a pH 2 using hydrochloric acid and then purified using ion-exchange chromatography (Dowex 50x-8, 100 meshcation) to provide 0.21 g of a yellow powder. Yield: 53% 1 H NMR (DMSO-d6): δ2.56 (S, 3H), 3.01 (m, 2H), 3.48 (t, 1H), 3.9 (dd, 2H) 7.05 (m, 1H), 7.13 (m, 3H). MS (FD): m/e 192 (M+2).

References:

US5491166,1996,A