Acetic Acid → HCID 20244647, compound

HRID 1663373Notes

Reaction equation

HRID 1663373 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[Br:13]Br.C(O)(=O)C>ClCCl.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[CH:4][C:5]([CH:6]=[O:7])=[CH:8][C:9]=1[Br:13]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 132377034-Amino-3-nitrobenzaldehyde

Product 1

HCID 20244647HCID 20244647, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Amino-3-nitro-benzaldehyde (2.1 g) was dissolved in 25 ml of dichloromethane. Bromine (2 ml) and acetic acid (1 ml) were added and the mixture was stirred for 2 h at room temperature. The mixture was diluted with ethyl acetate and washed with aq. NaHSO3. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silicagel in heptane/ethyl acetate 1/0→0/1 (v/v) as eluent.

Workup

  1. washwashed with aq. NaHSO3
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silicagel in heptane/ethyl acetate 1/0→0/1 (v/v) as eluent

Sources & evidence

ORD record
ord-3ff5366e9c904d7e90a0421c2e47d682
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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