Hydrochloric Acid → HCID 69951094, compound

HRID 648854Notes

Reaction equation

HRID 648854 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[ClH:15]>>[ClH:15].[NH2:12][C:11]1[C:2]([CH3:1])=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 601165Methyl 2-methyl-3-nitrobenzoate

Product 1

HCID 69951094HCID 69951094, compound

Procedure

To a stirred suspension of 185.6 g of stannous chloride dihydrate in concentrated hydrochloric acid (450 ml) at 15° was added 48.8 g of 2-methyl-3-nitrobenzoic acid, methyl ester. The temperature of the reaction mixture rose steadily to 63° before a cooling bath was applied. After the addition was complete, the solution was stirred at 40° to room temperature for 1.5 hours. The desired product was obtained by filtration of the reaction mixture at 7°, washing with ethyl acetate and n-butyl chloride, and drying. The yield of 3-amino-2-methylbenzoic acid, methyl ester, hydrochloride m.p. 220°-228°(dec.), was 60.8 g as a white solid.

Workup

  1. customThe temperature of the reaction mixture rose steadily to 63° before a cooling bath
  2. additionAfter the addition

Sources & evidence

ORD record
ord-9a381f70aabd4db0bf0238027feac8f8
Source dataset
uspto-grants-1988_04
Patent number
US04737185

Reaction notes

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