Formic Acid → HCID 19040638, compound

HRID 1683767Notes

Reaction equation

HRID 1683767 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[C:5]([C:14]#N)=[CH:4][CH:3]=1.C(O)=[O:17]>[Ni]>[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[C:5]([CH:14]=[O:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 284Formic Acid2×HCID 19040669HCID 19040669, compound

Product 1

HCID 19040638HCID 19040638, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst2×

Procedure

A solution of 9-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepine-6-carbonitrile (3.1 g, 14 mmol) in 90% formic acid (40 ml) was treated with Raney® nickel (3.1 g), stirred and heated to reflux for 3 hours. Additional Raney® nickel (17 g) and 90% formic acid (85 ml) were added over the next 12 hours and the mixture was stirred for an additional 3 hours. The mixture was cooled, filtered and the filter cake washed with 45% formic acid. The filtrate was concentrated, basified with 10% sodium hydroxide, extracted with ethyl acetate and the organic phase was washed, dried and concentrated to give 3 g of 9-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepine-6-carboxaldehyde.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. stirringthe mixture was stirred for an additional 3 hours
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. washthe filter cake washed with 45% formic acid
  7. concentrationThe filtrate was concentrated
  8. extractionextracted with ethyl acetate
  9. washthe organic phase was washed
  10. customdried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-8ffbb701fd9a4ffbaf9603f525ea189c
Source dataset
uspto-grants-1997_06
Patent number
US05639748

Reaction notes

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