Lithium borohydride → 4-Hexyl-6-hydroxymethyl-1,4-dihydro-quinoline-3-carbonitrile

HRID 1297681Notes

Reaction equation

HRID 1297681 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([C:16]#[N:17])=[C:9]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=O)C.[BH4-].[Li+]>>[CH2:18]([CH:9]1[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([CH2:4][OH:3])[CH:7]=2)[NH:12][CH:11]=[C:10]1[C:16]#[N:17])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

3

Reactant 2

HCID 4148881Lithium borohydrideHCID 585858293-Cyano-4-hexyl-quinoline-6-carboxylic acid ethyl ester

Product 1

HCID 585858074-Hexyl-6-hydroxymethyl-1,4-dihydro-quinoline-3-carbonitrile

Procedure

Similar procedure as described in example 46e was used, starting from 3-cyano-4-hexyl-quinoline-6-carboxylic acid ethyl ester (example 52a) and lithium borohydride to give 4-hexyl-6-hydroxymethyl-1,4-dihydro-quinoline-3-carbonitrile as a yellow solid. LC-MS m/e 271 (MH+).

Sources & evidence

ORD record
ord-a887cd5d74484e6c844982300de6e39a
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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