Sodium borohydride → 2,3-DiaMino-5-broMobenzoic acid Methyl ester

HRID 1470600Notes

Reaction equation

HRID 1470600 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([N+:11]([O-])=O)[C:5]=1[NH2:14].[BH4-].[Na+]>CO.O.[Ni](Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([NH2:11])[C:5]=1[NH2:14]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 17984898Methyl 2-amino-5-bromo-3-nitrobenzoate

Product 1

HCID 580739202,3-DiaMino-5-broMobenzoic acid Methyl ester

Reagents, catalysts & solvents 3

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-amino-5-bromo-3-nitro-benzoic acid methyl ester (5 g, 18.18 mmol) in methanol (15 mL) was added nickel chloride (10.8 g, 45.4 mmol) and was cooled to 0° C. To this cold solution, sodium borohydride (3.45 g, 90 mmol) was added in small portions. After the addition, the reaction mixture was diluted with water, extracted with ethyl acetate. The combined organic layers were dried, concentrated and the resulting residue was purified by column chromatography using 30% ethyl acetate in hexane to obtain the title compound as grey coloured solid.

Workup

  1. additionAfter the addition
  2. extractionextracted with ethyl acetate
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-f9f3a3bee5e6453e92c48be8632c9400
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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