Ammonia → Anthranilamide

HRID 262427Notes

Reaction equation

HRID 262427 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3].[NH3:13]>>[C:2]([NH2:13])(=[O:3])[C:1]1[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:6].[NH:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([OH:4])=[O:3])[C:5]([NH2:13])=[O:12]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 8359Isatoic Anhydride

Product 2

HCID 6942AnthranilamideHCID 53114732-(carbamoylamino)benzoic Acid

Procedure

prakt. Chem., [2], 30 (1884), 467 et seq., and J. org. Chem., 13 (1948), 347 et seq. and 24 (1959), 1,214 et seq. disclose that isatoic anhydride reacts with aqueous ammonia to give anthranilamide and o-ureidobenzoic acid. The reaction of 5,7-dichloroisatoic anhydride with ammonia gives 6,8-dichlorobenzoyleneurea (J. org. Chem., 3 (1938), 414 et seq., and 12 (1947), 743 et seq.), whilst other chlorine-substituted isatoic anhydrides give only moderate yields of chlorinated anthranilamides (J. Org. Chem., 26 (1961), 613 et seq.).

Sources & evidence

ORD record
ord-45813e86972945db8bf7a67892337e43
Source dataset
uspto-grants-1979_05
Patent number
US04154755

Reaction notes

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