Ammonia → 4-Amino-8-cyano-2,3,3a,9b-tetrahydro-1H-cyclopenta[c]quinoline

HRID 1937006Notes

Reaction equation

HRID 1937006 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=S)[CH:7]3[CH2:14][CH2:15][CH2:16][CH:6]3[C:5]=2[CH:4]=1)#[N:2].[NH3:17]>>[NH2:17][C:8]1[CH:7]2[CH2:14][CH2:15][CH2:16][CH:6]2[C:5]2[CH:4]=[C:3]([C:1]#[N:2])[CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 224624558-Cyano-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinoline-4-thione

Product 1

HCID 224624774-Amino-8-cyano-2,3,3a,9b-tetrahydro-1H-cyclopenta[c]quinolineYield 81%

Procedure

Analogously to Example 4, 8-cyano-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinoline-4-thione (40 mg, 0.18 mmol) is reacted with 7N methanolic ammonia solution (10 ml) to form 30 mg (81%) of product.

Sources & evidence

ORD record
ord-b293d3740d9b46f485f27a1ff98129ca
Source dataset
uspto-grants-2002_05
Patent number
US06391887B1

Reaction notes

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