Acetic Anhydride → HCID 178526764, compound

HRID 476152Notes

Reaction equation

HRID 476152 reaction equation
[Cl: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>>[Cl: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 668801485-Chloro-2-(2-nitrovinylamino)benzoic acid

Product 1

HCID 178526764HCID 178526764, compound

Procedure

5-Chloro-2-(2-nitrovinylamino)benzoic acid (Compound of step 1, 24 g, 98.36 mmol) and potassium acetate (19.2 g, 196.72 mmol) in acetic anhydride (120 mL, 1200 mmol) were stirred for 3 hours at 120° C. The precipitate was filtered, washed with acetic acid and water and dried in vacuo to obtain the title compound. Yield: 15 g (64%); 1H NMR (DMSO-d6, 300 MHz): δ 13.142 (s, 1H), 9.32 (s, 1H), 8.159-8.166 (d, 1H, J=2.1 Hz), 7.822-7.859 (dd, 1H, J=8.7 Hz, 2.4 Hz), 7.734-7.763 (d, 1H, J=8.7 Hz); MS: m/z 225 (M+).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with acetic acid and water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-19a9c942e00a41608328f866bc3a05f8
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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