Acetic Anhydride → HCID 12912434, compound

HRID 1680830Notes

Reaction equation

HRID 1680830 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][C:9]1[C:17]([CH3:18])=[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:15]([CH3:24])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12]>C(O)=O>[CH:1]([NH:8][C:9]1[C:17]([CH3:18])=[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:15]([CH3:24])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])=[O:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 12685839HCID 12685839, compound

Product 1

HCID 12912434HCID 12912434, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To 14.5 ml of 90% formic acid was added 30 ml of acetic anhydride. The mixture was warmed, and then heated to 50°-60° C. for two hours. To the mixture cooled to room temperature was added portionwise with stirring 15.0 g of 2-amino-4-ethoxycarbonyl-3,5-dimethylbenzoic acid. The mixture was further stirred at room temperature for 3 hours and poured into ice water. The resulting precipitate was filtered and recrystallized from ethyl acetate/n-hexane to yield 11.8 g (70.5% of theory) of 2-formylamino-4-ethoxycarbonyl-3,5-dimethylbenzoic acid melting at 144.5°-146° C.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureheated to 50°-60° C. for two hours
  3. additionwas added portionwise
  4. filtrationThe resulting precipitate was filtered
  5. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-ea5c1d27b0784dc7a1d2c2aaeb87b95d
Source dataset
uspto-grants-1981_06
Patent number
US04276295

Reaction notes

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