HCID 86659461, compound → HCID 67003319, compound

HRID 536425Notes

Reaction equation

HRID 536425 reaction equation
[NH2:1][C:2]1([C:10]([CH3:11])=[CH:9][C:8](Br)=[CH:7][CH:6]1[N+:13]([O-])=O)[C:3]([OH:5])=[O:4]>CO.[Pd]>[NH2:1][C:2]1([C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][CH:6]1[NH2:13])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 1

HCID 86659461HCID 86659461, compound

Product 1

HCID 67003319HCID 67003319, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-amino-4-bromo-6-methyl-2-nitrobenzoic acid (16 g) and Pd/C (3.2 g) in methanol (400 ml) was stirred under hydrogen (1 bar) for 48 h and filtered through Celite under nitrogen atmosphere. Evaporation of methanol and purification by chromatography (hexane/ethyl acetate 40:60) gave 1,2-diamino-6-methylbenzoic acid (6.7 g) as a brown solid (6.7 g). 1H-NMR (400 MHz, CDCl3): 12.09 (bs, 1H), 6.73 (d, 1H), 6.13 (d, 1H), 1.98 (s, 3H). LCMS: m/z=167.11 (M+H)

Workup

  1. filtrationfiltered through Celite under nitrogen atmosphere
  2. customEvaporation of methanol and purification by chromatography (hexane/ethyl acetate 40:60)

Sources & evidence

ORD record
ord-849ab9ee41304ac5b73be2a30cb284ab
Source dataset
uspto-grants-2014_10
Patent number
US08859592B2

Reaction notes

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