Trifluoroacetic anhydride → 5-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide

HRID 637344Notes

Reaction equation

HRID 637344 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]([NH2:15])=[O:14])=[C:6]([CH2:8][C:9](O)=[O:10])[CH:7]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:12]([C:13]([NH2:15])=[O:14])[C:9](=[O:10])[CH2:8]2

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 136476552-(5-Chloro-2-ureidophenyl)acetic acid

Product 1

HCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamideYield 1.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Cyclization of 4.78 g (0.021 mole) of 2-(5-chloro-2-ureidophenyl)acetic acid with 8.0 g (0.063 mole) of trifluoroacetic anhydride in 75 ml of trifluoroacetic acid, according to the method of Example 13, followed by recrystallization of the crude product from acetonitrile, gave 80 mg of the title compound, m.p. 211° C. (dec.).

Workup

  1. customfollowed by recrystallization of the crude product from acetonitrile

Sources & evidence

ORD record
ord-dc73f182a51a4b2888b213ef6c85235b
Source dataset
uspto-grants-1985_12
Patent number
US04556672

Reaction notes

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