6,7-Dihydro-5H-quinoline-8-one → HCID 178420731, compound

HRID 1592638Notes

Reaction equation

HRID 1592638 reaction equation
[N:1]1[C:10]2[C:9](=O)[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH:12]1[CH:16]=[C:15]([CH2:17][CH2:18][NH2:19])[N:14]=[CH:13]1>CO.[BH4-].[Na+]>[NH:12]1[CH:16]=[C:15]([CH2:17][CH2:18][NH:19][CH:9]2[C:10]3[N:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH2:6][CH2:7][CH2:8]2)[N:14]=[CH:13]1

Participants

5

Reactant 2

HCID 117447776,7-Dihydro-5H-quinoline-8-oneHCID 178419017HCID 178419017, compound

Product 1

HCID 178420731HCID 178420731, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 4311764Sodium borohydrideSolvent

Procedure

Using General Procedure B: Reaction of 6,7-dihydro-5H-quinolin-8-one in MeOH, 2-(1H-imidazol-4-yl)-ethylamine and NaBH4 gave [2-(1H-imidazol-4-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine. 1H NMR (CDCl3) δ 1.75 (m, 2H), 1.91 (m, 1H), 2.10 (m, 1H), 2.72 (q, 2H, J=8.6 Hz), 2.82 (q, 2H, J=10.0 Hz), 3.01 (t, 2H, J=6.6 Hz), 3.81 (t, 1H, J=6.1 Hz), 6.73 (s, 1H), 7.04 (q, 1H, J=4.3 Hz), 7.35 (d, 1H, J=7.6 Hz), 7.43 (s, 1H), 8.36 (d, 1H, J=4.0 Hz).

Sources & evidence

ORD record
ord-302676f311f14318905832433a3ad4b4
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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