Hydroxyamine hydrochloride → 3-trifluoracetyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-carbaldehyde oxime

HRID 33206Notes

Reaction equation

HRID 33206 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]([CH:16]=O)=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].Cl.[NH2:21][OH:22]>N1C=CC=CC=1>[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]=[N:21][OH:22])=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 582779543-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7-carbaldehyde

Product 1

HCID 1317270753-trifluoracetyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-carbaldehyde oximeYield 81.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Trifluoracetyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-carbaldehyde (20.0 g) and hydroxylamine hydrochloride (6.1 g) in pyridine (140 ml) were stirred overnight and the reaction then evaporated in vacuo. The residue was partitioned between ethyl acetate and 10% sodium carbonate solution and the combined organic layers dried and evaporated to give 3-trifluoracetyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-carbaldehyde oxime (17.2 g) as a yellow solid.

Workup

  1. customthe reaction
  2. customthen evaporated in vacuo
  3. customThe residue was partitioned between ethyl acetate and 10% sodium carbonate solution
  4. customthe combined organic layers dried
  5. customevaporated

Sources & evidence

ORD record
ord-49730e9d86ed432089edb9d0712f839e
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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