4-(Trifluoromethoxy)phenylhydrazine hydrochloride → 8-(Trifluoromethoxy)-5,10-dihydroindeno[1,2-b]indole-1-carboxylic acid

HRID 1595469Notes

Reaction equation

HRID 1595469 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.[F:15][C:16]([F:27])([F:26])[O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24]N)=[CH:20][CH:19]=1>>[F:15][C:16]([F:26])([F:27])[O:17][C:18]1[CH:19]=[CH:20][C:21]2[NH:24][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:22]=2[CH:23]=1

Participants

3

Reactant 2

HCID 27773284-(Trifluoromethoxy)phenylhydrazine hydrochlorideHCID 125422061-Oxo-indan-4-carboxylic acid

Product 1

HCID 224628208-(Trifluoromethoxy)-5,10-dihydroindeno[1,2-b]indole-1-carboxylic acidYield 8.5%

Procedure

In a manner similar to Example 17, 1-oxo-indan-4-carboxylic acid (1.00 g, 5.68 mmol) and 4-trifluoromethoxyphenylhydrazine hydrochloride (1.30 g, 5.68 mmol) were converted to the title compound (0.160 g, 8%) as an light tan solid: mp 256-265 (dec)° C.; 1H NMR (DMSO-d6): δ 4.03 (s, 2H), 7.05-7.08 (m, 1H), 7.49 (d, 1H), 7.53 (d, 1H), 7.61 (d, 1H), 7,79-7.83 (m, 2H), 11.92 (s, 1H), 13.08 (s, 1H); MS [EI, m/z]: 333 [M]+.

Sources & evidence

ORD record
ord-3892bafb143e41da9fd20e4165dbb6c8
Source dataset
uspto-grants-2001_09
Patent number
US06288099B1

Reaction notes

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