2,3,4,5-tetrahydro-1H-1-benzazepine → 313667-22-0

HRID 1292906Notes

Reaction equation

HRID 1292906 reaction equation
[N:1]([O-:3])=O.[Na+].[NH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][CH2:7][CH2:6]1>O.CC(O)=O>[N:1]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:3]

Participants

5

Reactant 2

HCID 5765032,3,4,5-tetrahydro-1H-1-benzazepineHCID 23668193Sodium Nitrite

Product 1

HCID 21859610313667-22-0Yield 91%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A solution of sodium nitrite (1.35 g, 19.6 mmol) in water (4.0 mL) was added dropwise to a solution of 2,3,4,5-tetrahydro-1H-1-benzazepine (2.40 g, 16.3 mmol) in AcOH (10 mL) at 0-10° C. The mixture was stirred at 5° C. for 10 min, room temperature for 1 h and extracted with CH2Cl2 (3×20 mL). The organic layer was dried (MgSO4), concentrated in vacuo and flash column chromatography (EtOAc:hexane/1:9) gave 1-nitroso-2,3,4,5-tetrahydro-1H-1-benzazepine (2.60 g, 91%) as a brown liquid. 1H NMR (CDCl3, 300 MHz) δ 1.70-1.85 (m, 4H), 2.70-2.82 (m, 2H), 3.92 (br, 2H), 7.25-7.32 (m, 1H), 7.32-7.40 (m, 2H), 7.40-7.48 (m, 1H) ppm.

Workup

  1. extractionextracted with CH2Cl2 (3×20 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo and flash column chromatography (EtOAc:hexane/1:9)

Sources & evidence

ORD record
ord-ac317df089a0407090912ff98b212e64
Source dataset
uspto-grants-2007_07
Patent number
US07238690B2

Reaction notes

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