1H-imidazole-2-carbaldehyde → 1-(1H-Imidazol-2-ylmethyl)-7-methoxy-1,2,3,4-tetrahydro-quinoline

HRID 1172996Notes

Reaction equation

HRID 1172996 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][NH:10]2)=[CH:5][CH:4]=1.[NH:13]1[CH:17]=[CH:16][N:15]=[C:14]1[CH:18]=O.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[NH:13]1[CH:17]=[CH:16][N:15]=[C:14]1[CH2:18][N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 249551H-imidazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 162443887-Methoxy-1,2,3,4-tetrahydroquinoline

Product 1

HCID 595568131-(1H-Imidazol-2-ylmethyl)-7-methoxy-1,2,3,4-tetrahydro-quinoline

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

Prepared analogously to Example 1, from 7-methoxy-1,2,3,4-tetrahydro-quinoline, imidazole-2-carboxaldehyde, zinc chloride and sodium cyanoborohydride in methanol. MS (ISP): 244.4 ([M+H]+).

Sources & evidence

ORD record
ord-bd5711f603b14025b38df7ae597b5f1b
Source dataset
uspto-grants-2010_11
Patent number
US07834044B2

Reaction notes

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