Isoamyl Nitrite → 1-(Hydroxyimino)-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

HRID 2376615Notes

Reaction equation

HRID 2376615 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[CH2:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[CH2:4][CH2:3]1.C([O:19][N:20]=O)CC(C)C.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[OH:19][N:20]=[C:7]1[C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[CH2:4][CH2:3][N:2]([CH3:1])[C:8]1=[O:9]

Participants

5

Reactant 3

HCID 8053Isoamyl NitriteHCID 8521743-methyl-4,5-dihydro-1H-benzo[d]azepin-2(3H)-oneHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 713578231-(Hydroxyimino)-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-Methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one (1 eq.) was dissolved in THF and isoamylnitrite (1.2 eq.) was added. The mixture was cooled to 0° C. in an ice bath. NaHMDS (1.1 eq., 1M in THF) was added dropwise. After stirring for 1 hour or until the reaction was complete, the mixture was concentrated then acidified with 1N aqueous hydrochloric acid solution and extracted with ethyl acetate. The organic portion was dried and concentrated to yield a crude product which was purified by silica gel chromatography to give 1-hydroxyimino-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one: Mass spectroscopy (M+H)+, 205.1.

Workup

  1. concentrationthe mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. customThe organic portion was dried
  4. concentrationconcentrated
  5. customto yield a crude product which
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-029e075b6b82400587ba9363131c576c
Source dataset
uspto-grants-2008_12
Patent number
US07468365B2

Reaction notes

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