5-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxamide → 9-(4-butylphenyl)-6,11-dihydro-5H-benzo[a]carbazole-3-carboxamide

HRID 1690688Notes

Reaction equation

HRID 1690688 reaction equation
O=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([NH2:14])=[O:13])[CH:5]=[CH:4][C:3]1=2.Cl.[CH2:16]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([NH:32]N)[CH:27]=2)=[CH:22][CH:21]=1)[CH2:17][CH2:18][CH3:19]>>[CH2:16]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[C:28]3[C:29]([C:11]4[CH2:10][CH2:9][C:8]5[CH:7]=[C:6]([C:12]([NH2:14])=[O:13])[CH:5]=[CH:4][C:3]=5[C:2]=4[NH:32]3)=[CH:30][CH:31]=2)=[CH:22][CH:21]=1)[CH2:17][CH2:18][CH3:19]

Participants

3

Reactant 2

HCID 221477905-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxamideHCID 66904838(4'-Butyl-biphenyl-3-yl)-hydrazine hydrochloride

Product 1

HCID 445790739-(4-butylphenyl)-6,11-dihydro-5H-benzo[a]carbazole-3-carboxamide

Procedure

The 5-Oxo-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid amide and (4′-Butyl-biphenyl-3-yl)-hydrazine hydrochloride (example 70, step 1) are reacted in the same manner and similar yield as example 1, step 3.11H NMR (400 MHz, d6-DMSO) δ 11.60 (s, 1H), 7.83 (m, 2H), 7.70 (d, J=8.3 Hz, 1H), 7.59 (m, 3H), 7.27-7.35 (m, 4H), 3.05 (m, 2H), 2.96 (m, 2H), 2.62 (m, 2H), 1.60 (m, 2H), 1.35 (m, 2H), 0.92 (m, 3H); LC/MS calculated for [M+H]+ C27H27N2O: 395.5, found: 395.1.

Workup

  1. customsimilar yield as example 1, step 3.11H NMR (400 MHz, d6-DMSO) δ 11.60 (s, 1H), 7.83 (m, 2H), 7.70 (d, J=8.3 Hz, 1H), 7.59 (m, 3H), 7.27-7.35 (m, 4H), 3.05 (m, 2H), 2.96 (m, 2H), 2.62 (m, 2H), 1.60 (m, 2H), 1.35 (m, 2H), 0.92 (m, 3H)

Sources & evidence

ORD record
ord-5e32e58d70ee466099a3c9a75b74e3be
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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