4-Hexyl-6-hydroxymethyl-1,4-dihydro-quinoline-3-carbonitrile → 6-Formyl-4-hexyl-quinoline-3-carbonitrile

HRID 1297682Notes

Reaction equation

HRID 1297682 reaction equation
[CH2:1]([CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][OH:18])[CH:15]=2)[NH:10][CH:9]=[C:8]1[C:19]#[N:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>[O-2].[O-2].[Mn+4]>[CH:17]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:19]#[N:20])=[C:7]2[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[O:18]

Participants

3

Reactant 1

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

Product 1

HCID 585858586-Formyl-4-hexyl-quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

Similar procedure as described in example 46f was used, starting from 4-hexyl-6-hydroxymethyl-1,4-dihydro-quinoline-3-carbonitrile (example 52b) and manganese dioxide to give 6-formyl-4-hexyl-quinoline-3-carbonitrile as a white solid. LC-MS m/e 267 (MH+).

Sources & evidence

ORD record
ord-08f31e9f5dfb436695b6a6269176d754
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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