Ozone → 5-(Benzyloxy)quinoline-6-carbaldehyde

HRID 47955Notes

Reaction equation

HRID 47955 reaction equation
[CH2:1]([O:8][C:9]1[C:18](/[CH:19]=C/C)=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:22]=[O+][O-].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:18]([CH:19]=[O:22])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24823OzoneHCID 81531DiisopropylethylamineHCID 234318255-(benzyloxy)-6-[(1E)-prop-1-enyl]quinoline

Product 1

HCID 234318215-(Benzyloxy)quinoline-6-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treatment of 5-(benzyloxy)-6-[(1E)-prop-1-enyl]quinoline in methylene chloride with excess ozone at −78° C. followed by addition of diisopropylethylamine, aqueous work-up, and subsequent purification by flash column chromatography provides 5-(benzyloxy)quinoline-6-carbaldehyde.

Sources & evidence

ORD record
ord-af7ca252dadf4d2ebcf7ebef43cb0b45
Source dataset
uspto-grants-2004_03
Patent number
US06700001B2

Reaction notes

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