Anthranilic Acid → N-Formylanthranilic acid

HRID 1977670Notes

Reaction equation

HRID 1977670 reaction equation
C1(C)C=CC=CC=1.[C:8]([OH:17])(=[O:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH2:11].[CH:18](O)=[O:19]>CCCCCC>[CH:18]([NH:11][C:10]1[C:9](=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([OH:17])=[O:16])=[O:19]

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 284Formic AcidHCID 1140Toluene

Product 1

HCID 101399N-Formylanthranilic acid

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A toluene (1100 ml) solution of anthranilic acid (205.5 g) and formic acid (170 ml) was heated under reflux for 4.5 hours. After the solution was allowed to cool, hexane was added to crystals deposited. The crystals were collected by filtration and washed with hexane. The resulting crystals were dried at 110° C. under reduced pressure to obtain N-formyl-anthranilic acid (244.0 g, crude product) as white crystals.

Workup

  1. temperatureunder reflux for 4.5 hours
  2. temperatureto cool
  3. filtrationThe crystals were collected by filtration
  4. washwashed with hexane
  5. customThe resulting crystals were dried at 110° C. under reduced pressure

Sources & evidence

ORD record
ord-ca4e60b87f72445bbc7632106119707b
Source dataset
uspto-grants-2001_05
Patent number
US06235730B1

Reaction notes

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