4-Chloro-3-hydrazinylbenzoic acid hydrochloride → 8-Chloro-2-(2-methoxyphenyl)-1,3,4,5-tetrahydrobenz[cd]indol-5-one

HRID 1637283Notes

Reaction equation

HRID 1637283 reaction equation
Cl.[C:2]([C:5]1[CH:6]=[CH:7][C:8]([Cl:13])=[C:9]([NH:11]N)[CH:10]=1)([OH:4])=O.[CH3:14][O:15][C:16]1[CH:29]=[CH:28][CH:27]=[CH:26][C:17]=1[C:18]([CH:20]([CH2:24][CH3:25])C(O)=O)=O>>[Cl:13][C:8]1[C:9]2[NH:11][C:18]([C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=3[O:15][CH3:14])=[C:20]3[CH2:24][CH2:25][C:2](=[O:4])[C:5]([C:10]=23)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 162429964-Chloro-3-hydrazinylbenzoic acid hydrochlorideHCID 19348145(2-Methoxybenzoyl)butyric acid

Product 1

HCID 193482768-Chloro-2-(2-methoxyphenyl)-1,3,4,5-tetrahydrobenz[cd]indol-5-oneYield 12%

Procedure

The procedure of Example 60, steps 1 to 3 was repeated using (5-carboxy-2-chlorophenyl)hydrazine hydrochloride (24.1 g) and (2-methoxybenzoyl)butyric acid (16 g) to yield 2.45 g (12%) of the titled compound as a yellow powder.

Sources & evidence

ORD record
ord-1414ce30e24c4f2885b9612b6672c35d
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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