Benzoic acid, 4-amino-3-nitro- → 4-Amino-3-bromo-5-nitrobenzoic acid

HRID 592317Notes

Reaction equation

HRID 592317 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[Br:14]NC(=O)CCC(N)=O>ClCCl.CN(C)C=O>[NH2:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:9][C:10]=1[Br:14]

Participants

5

Reactant 2

HCID 74115Benzoic acid, 4-amino-3-nitro-HCID 9834204N-Bromosuccinamide

Product 1

HCID 547587704-Amino-3-bromo-5-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-3-nitrobenzoic acid (2.50 g, 13.7 mmol) in dichloromethane (65.4 mL) and N,N-dimethylformamide (3.3 mL) was added N-bromosuccinamide (2.69 g, 15.1 mmol). The mixture was stirred at ambient temperature. After 15 min, the mixture was quenched with saturated sodium sulfite. Hydrochloric acid (1.0 M) was added and the mixture was extracted with dichloromethane. The combined organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated (3.65 g). LC-MS [M]=261.0.

Workup

  1. customthe mixture was quenched with saturated sodium sulfite
  2. additionHydrochloric acid (1.0 M) was added
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated (3.65 g)

Sources & evidence

ORD record
ord-bd61b728cc4b485bba95427f26a8d8f8
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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