Acetic Anhydride → HCID 178526759, compound

HRID 476147Notes

Reaction equation

HRID 476147 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][CH:12]=[CH:13][N+:14]([O-:16])=[O:15])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C([O-])(=O)C.[K+].C(OC(=O)C)(=O)C>>[Br:1][C:2]1[CH:10]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:11]=[CH:12][C:13]([N+:14]([O-:16])=[O:15])=[C:7]2[OH:8]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517044Potassium AcetateHCID 534050555-Bromo-2-(2-nitrovinylamino)benzoic acid

Product 1

HCID 178526759HCID 178526759, compound

Procedure

5-Bromo-2-(2-nitrovinylamino)benzoic acid (Compound of step 1, 25 g, 87 mmol) and potassium acetate (10.5 g, 104 mmol) in acetic anhydride (112 mL, 1185 mmol) were stirred for 3 hours at 120° C. The precipitate was filtered, and washed with acetic acid till the filtrate was colorless. It was further washed with water and dried to obtain the title compound. Yield: 15 g (64%); 1H NMR (CDCl3, 500 MHz): δ 9.275 (s, 1H), 8.611-8.615 (d, 1H, J=2 Hz), 8.100-8.118 (d, 1H, J=9 Hz), 8.026-8.048 (dd, 1H, J=8.5 Hz, 2 Hz).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with acetic acid till the filtrate
  3. washIt was further washed with water
  4. customdried

Sources & evidence

ORD record
ord-e6f84824a38a418d8be2ef1c97c2e206
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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