3-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile → 3-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carboxaldehyde

HRID 235592Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([CH3:14])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[C:12]#N.[H-].C([Al+]CC(C)C)C(C)C.C(C1C([O:34]C)=NC(C)=CC=1)#N>>[Cl:1][C:2]1[N:3]=[C:4]([CH3:14])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH:12]=[O:34]

Participants

Reactant 3

HCID 37301863-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile

HCID 53238032-Methoxy-6-methylnicotinonitrile

HCID 21225700Diisobutylaluminumhydride

Product 1

HCID 139353363-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carboxaldehyde

Procedure

3-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carboxaldehyde was prepared from 3-chloro-4-cyano-methyl-5,6,7,8-tetrahydroisoquinoline by reduction with diisobutylaluminium hydride following essentially the same procedure as that described in J. Org. chem., 1980, 45, 1354 for the reduction of 3-cyano-2-methoxy-6-methylpyridine. Pmr spectrum (CDCl3 ; δ in ppm): 1.79 (4H,m); 2.47 (3H,s); 2.59-3.18 (4H,m); 10.52 (1H,s).

Sources & evidence

ORD record: ord-487cc02b608140c5ac7a3e3fe2affa87
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04640708

Reaction notes

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