Water → Methyl 3,4-dihydro-4-methyl-2H-1,4-benzoxazine-5-carboxylate

HRID 560278Notes

Reaction equation

HRID 560278 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[O:20][CH2:19][CH2:18][NH:17][C:16]=12)=[O:10].CI.O>CN(C=O)C.CCOC(C)=O>[CH3:7][O:8][C:9]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[O:20][CH2:19][CH2:18][N:17]([CH3:1])[C:16]=12)=[O:10]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14373654Methyl 3,4-dihydro-2H-1,4-benzoxazine-5-carboxylate

Product 1

HCID 14373655Methyl 3,4-dihydro-4-methyl-2H-1,4-benzoxazine-5-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

K2CO3 (1.79 mmol) is added to a solution of 3,4-dihydro-2H-benzo[1,4]oxazine-5-carboxylic acid methyl ester (0.78 mmol) in DMF (1.0 mL). After 30 min methyl iodide (1.55 mmol) is added and the mixture is stirred for 2 h at 75° C. Cold water and EtOAc are added, the layers are separated and the aq. layer is extracted with EtOAc. The combined organic layers are washed with water and brine, dried over MgSO4 and concentrated in vacuo to give a crude product which is used without further purification. LC-MS: tR=0.71 min; [M+H]+=208.1.

Workup

  1. customthe layers are separated
  2. extractionthe aq. layer is extracted with EtOAc
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b23026c11404401b7e3f154fe32f8c1
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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