Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → 8-Chloro-5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acid

HRID 1595468Notes

Reaction equation

HRID 1595468 reaction equation
O=[C:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([OH:13])=[O:12])[C:5]=2[CH2:4][CH2:3]1.Cl.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22]N)=[CH:18][CH:17]=1>>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]2[NH:22][C:2]3[C:10]4[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([OH:13])=[O:12])[C:5]=4[CH2:4][C:3]=3[C:18]=2[CH:17]=1

Participants

3

Reactant 2

HCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 125422061-Oxo-indan-4-carboxylic acid

Product 1

HCID 224628258-Chloro-5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acidYield 14.3%

Procedure

In a manner similar to Example 17, 1-oxo-indan-4-carboxylic acid (1.00 g, 5.68 mmol) and 4-chlorophenylhydrazine hydrochloride (1.03 g, 5.75 mmol) were converted to the title compound (0.230 g, 14%) as a pale brown solid: mp>300° C.; 1H NMR (DMSO-d6,): δ 4.00 (s, 2H), 7.10 (d of d, 1H), 7.46 (d, 1H), 7.51 ( d, 1H), 7.66 (d, 1H), 7.78-7.81 (m, 2H), 11.83 (s, 1H), 13.57 (s, 1H); MS [EI, m/z]: 283 [M]+.

Sources & evidence

ORD record
ord-eca00823e1d84188a87f8f3981f2eade
Source dataset
uspto-grants-2001_09
Patent number
US06288099B1

Reaction notes

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