Water → Methyl 2-Amino-4-bromobenzoate

HRID 2353870Notes

Reaction equation

HRID 2353870 reaction equation
[Sn](Cl)Cl.[Br:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([N+:15]([O-])=O)[CH:6]=1.O.[OH-].[K+]>Cl>[NH2:15][C:7]1[CH:6]=[C:5]([Br:4])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24479Stannous ChlorideHCID 18350461Methyl 4-bromo-2-nitrobenzoate

Product 1

HCID 17871390Methyl 2-Amino-4-bromobenzoateYield 84.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Add tin(II) chloride (65.9 g, 292 mmol) to a suspension of methyl 4-bromo-2-nitrobenzoate (15.2 g, 58.4 mmol) in concentrated hydrochloric acid (120 mL) at room temperature and stir for 24 h. Slowly pour the mixture into water (700 mL) and adjust the pH to 9 with solid potassium hydroxide. Filter the white suspension through Celite, then stir the filter cake with ethyl acetate and filter that suspension. Separate the filtrate and extract the aqueous layer with ethyl acetate (200 mL). Combine the organic layers, dry over sodium sulfate, filter and remove the solvent under reduced pressure to afford the title compound as an off-white solid (11.3 g, 84%)

Workup

  1. filtrationFilter the white suspension through Celite
  2. stirringstir the filter cake with ethyl acetate
  3. filtrationfilter that suspension
  4. customSeparate the filtrate
  5. extractionextract the aqueous layer with ethyl acetate (200 mL)
  6. dry with materialCombine the organic layers, dry over sodium sulfate
  7. filtrationfilter
  8. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-d579340d7abf4e1d9700e9ca514a6976
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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