Acetic Anhydride → HCID 178423389, compound

HRID 476156Notes

Reaction equation

HRID 476156 reaction equation
[CH3:1][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>>[CH3:1][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 668814915-Methyl-2-(2-nitrovinylamino)benzoic acid

Product 1

HCID 178423389HCID 178423389, compound

Procedure

5-Methyl-2-(2-nitrovinylamino)benzoic acid (Compound of step 1, 1.5 g, 6.756 mmol) and potassium acetate (1.3 g, 13.51 mmol) were stirred in acetic anhydride (8 ml, 148 7 mmol) for 3 hours at 120° C. The precipitate was filtered and washed with acetic acid until the filtrate is colorless and then washed with water and dried in vacuo to obtain the title compound. Yield: 610 mg (64%); 1H NMR (DMSO-d6, 300 MHz): δ 9.126 (s, 1H), 8.035 (s, 1H), 7.606 (s, 2H), 2.432 (s, 3H); MS: m/z 203 (M−1).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with acetic acid until the filtrate
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-af05ba823cf24430bc1fd0977266a1e3
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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