Formic Acid → 3-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7-carbaldehyde

HRID 33205Notes

Reaction equation

HRID 33205 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][C:14]([C:16]#N)=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].C(O)=[O:21]>[Al].[Ni]>[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][C:14]([CH:16]=[O:21])=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 866536353-(2,2,2-Trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7-carbonitrile

Product 1

HCID 582779543-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6336846Nickel aluminideCatalyst

Procedure

3-Trifluoracetyl-7-cyano-2,3,4,5-tetrahydro-1H-3-benzazepine (20.3 g) and nickel-aluminium alloy (35.5 g) in 75% aq. formic acid (400 ml) were heated at 80° C. for 3 h. The reaction was allowed to cool, filtered and the filtrate extracted with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate solution, dried and evaporated to give 3-trifluoracetyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-carbaldehyde (20.0 g) as a yellow oil.

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. extractionthe filtrate extracted with ethyl acetate
  4. washThe combined organic layers were washed with saturated sodium bicarbonate solution
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-d36d0a924f1d4a71acc735d20c1b7ca8
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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