Formic Acid → 3-(2-(7-Chloroquinolin-2-yl)ethyl)benzaldehyde

HRID 232425Notes

Reaction equation

HRID 232425 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][CH2:13][C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[C:17]#N)=[N:9]2)=[CH:4][CH:3]=1.C(O)=[O:23]>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][CH2:13][C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH:17]=[O:23])=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 99945063-(2-(7-Chloroquinolin-2-yl)ethyl)benzonitrile

Product 1

HCID 104472473-(2-(7-Chloroquinolin-2-yl)ethyl)benzaldehyde

Procedure

To the cyanide (Step 1, 10 g) in formic acid (200 mL) at 100° was added portionwise Ni-Al alloy (3 g). The reaction mixture was heated at 110° for 6 hrs, filtered and evaporated. The residue was partitioned between NaHCO3 (aq) and ethyl acetate, and the organic layer was dried and evaporated. Flash chromatography using 30% ether in hexane afforded the title compound.

Workup

  1. temperatureThe reaction mixture was heated at 110° for 6 hrs
  2. filtrationfiltered
  3. customevaporated
  4. customThe residue was partitioned between NaHCO3 (aq) and ethyl acetate
  5. customthe organic layer was dried
  6. customevaporated

Sources & evidence

ORD record
ord-a90a4a6819c8432c8070469e10557794
Source dataset
uspto-grants-1989_07
Patent number
US04851409

Reaction notes

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