Water → 6-Methoxy-3,4-dihydro-2H-1,4-benzoxazine

HRID 1167609Notes

Reaction equation

HRID 1167609 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH2:9][N:8](C(=O)C)[C:7]=2[CH:15]=1.O.[OH-].[K+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH2:9][NH:8][C:7]=2[CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 22993340HCID 22993340, compound

Product 1

HCID 162444606-Methoxy-3,4-dihydro-2H-1,4-benzoxazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The compound obtained in Step C (1.5 g; 7.26 mmol) is dissolved in 7 ml of methanol, and then water (14 eq.; 101.6 mmol; 1.9 ml) and potassium hydroxide (6 eq.; 43.5 mmol; 2.44 g) are added. The solution is stirred vigorously at 60° C. for 2 hours. After extraction three times with dichloromethane, the organic phase is dried over MgSO4 and then removed under reduced pressure. The residue obained is purified by flash chromatography on silica gel (eluant: PE/AcOEt (1/1)). The title product is obtained in the form of a red solid.

Workup

  1. extractionAfter extraction three times with dichloromethane
  2. dry with materialthe organic phase is dried over MgSO4
  3. customremoved under reduced pressure
  4. customThe residue obained is purified by flash chromatography on silica gel (eluant: PE/AcOEt (1/1))

Sources & evidence

ORD record
ord-f087d9ce4ece467bbf58fbc696f21d80
Source dataset
uspto-grants-2003_09
Patent number
US06620809B2

Reaction notes

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