5-Tetralinylamine → 1H-Benz[g]indole-2,3-dione

HRID 1374812Notes

Reaction equation

HRID 1374812 reaction equation
[C:1]1([NH2:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.N1C2C(=CC=C3CCCC3=2)[C:14](=[O:24])[C:13]1=[O:25]>>[CH:7]1[CH:6]=[C:5]2[CH:4]=[CH:3][C:2]3[C:13](=[O:25])[C:14](=[O:24])[NH:11][C:1]=3[C:10]2=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 166715-TetralinylamineHCID 148855691,6,7,8-Tetrahydrocyclopenta[g]indole-2,3-dione

Product 1

HCID 1999681H-Benz[g]indole-2,3-dioneYield 54%

Procedure

The benz[g]isatin was prepared in two steps from 5,6,7,8-tetrahydro-1-naphthylamine using the methods described for 1,6,7,8-tetrahydrocyclopenta[g]indole-2,3-dione (G. W. Rewcastle et. al., J. Med. Chem., 1991, 34, 217). The product (54% yield from N-[1-(5,6,7,8-tetrahydronaphthalenyl)]-2-(hydroximino)acetamide) was obtained as an orange solid: mp. 234–235° C. (lit. [U.S. Pat. No. 1,856,210, 1929] 232° C.); NMR δH (400 MHz, DMSO-d6) 1.73 (4H, m), 2.49 (2H, m), 2.73 (2H, m), 6.78 (1H, d, J 7.7 Hz), 7.21 (1H, d, J 7.7 Hz) and 10.92 (1H, s).

Sources & evidence

ORD record
ord-c54fbb5f07874c01a77103a5f98b549b
Source dataset
uspto-grants-2007_01
Patent number
US07166613B2

Reaction notes

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