4-Fluorophenylhydrazine hydrochloride → 8-Fluoro-5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acid

HRID 1595467Notes

Reaction equation

HRID 1595467 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]1[CH:21]=[CH:20][C:19]([NH:22]N)=[CH:18][CH:17]=1>>[F: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 699814-Fluorophenylhydrazine hydrochlorideHCID 125422061-Oxo-indan-4-carboxylic acid

Product 1

HCID 224628158-Fluoro-5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acidYield 10%

Procedure

In a manner similar to Example 17, 1-oxo-indan-4-carboxylic acid (1.00 g, 5.68 mmol) and 4-fluorophenylhydrazine hydrochloride (0.923 g, 5.68 mmol) were converted to the title compound (0.140 g, 10%) as an off-white solid: mp>300° C.; 1H NMR (DMSO-d6): δ 3.98 (s, 2H), 6.93 (d of t, 1H), 7.38 (d of d, 1H), 7.44 (d of d, 1H), 7.50 (d, 1H), 7.77-7.80 (m, 2H), 11.72 (s, 1H), 13.43 (s, 1H); MS [EI, m/z]: 267 [M]+.

Sources & evidence

ORD record
ord-e7530a0a309b43be9f4b1f42a76063cd
Source dataset
uspto-grants-2001_09
Patent number
US06288099B1

Reaction notes

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