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

HRID 1595471Notes

Reaction equation

HRID 1595471 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.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22]N)=[CH:18][CH:17]=1>>[Br: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 121574-Bromophenylhydrazine hydrochlorideHCID 125422061-Oxo-indan-4-carboxylic acid

Product 1

HCID 224628038-Bromo-5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acid

Procedure

In a manner similar to Example 17, 1-oxo-indan4-carboxylic acid and 4-bromophenylhydrazine hydrochloride were reacted to form 8-bromo-5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acid which was converted to the ethyl ester in a manner similar to that described in Example 22 to afford the title compound as a tan solid: mp 198-200° C.; 1H NMR (DMSO-d6): δ 1.39 (t, 3H), 4.00 (s, 2H), 4.37 (q, 2H), 7.22 (d, 1H), 7.42 (d, 1H), 7.52 (t, 1H), 7.79-7.84 (m, 3H), 11.86 (s, 1H); MS [EI, m/z]: 355 [M]+.

Sources & evidence

ORD record
ord-903589003d2c4a91a81389c574480cdb
Source dataset
uspto-grants-2001_09
Patent number
US06288099B1

Reaction notes

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