Methanol → 6-Bromo-4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 2263543Notes

Reaction equation

HRID 2263543 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=O)[N:7]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:6]=2[CH:17]=1.CO>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 231485196-bromo-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 669007386-Bromo-4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

The solution of 2.85 g of 6-bromo-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one in 50 ml of tetrahydrofuran is admixed with 48 ml of 1M borane-tetrahydrofuran complex and stirred at 65° C. over 1 hour. The reaction mixture is cooled to room temperature and then admixed cautiously with 100 ml of methanol. After 10 minutes, the mixture is concentrated to dryness and the title compound is obtained as a yellowish oil from the residue by means of flash chromatography (SiO2 60 F). Rf=0.31 (1:2 EtOAc-heptane). Rt=4.89 (gradient I).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. waitAfter 10 minutes
  3. concentrationthe mixture is concentrated to dryness

Sources & evidence

ORD record
ord-e01b132046f14db8b094eab36751ac2d
Source dataset
uspto-grants-2010_12
Patent number
US07851634B2

Reaction notes

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