Chloroacetyl chloride → Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate

HRID 560271Notes

Reaction equation

HRID 560271 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[CH3:6][O:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[C:10]=1[OH:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:6][O:7][C:8]([C:9]1[C:10]2[O:16][CH2:2][C:3](=[O:4])[NH:15][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:17]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 12782444Methyl 3-amino-2-hydroxybenzoate

Product 1

HCID 23770643Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At RT chloro-acetyl chloride (29.0 mmol) is added dropwise to a solution of 3-amino-2-hydroxy-benzoic acid methyl ester (26.4 mmol) in DMF (100 mL). After 20 min K2CO3 (126 mmol) is added portionwise, the mixture is stirred for 16 h at RT and the solvents are removed in vacuo. Water and DCM are added, the layers are separated and the organic layer is washed with brine and dried over Na2SO4. The solvents are removed in vacuo to give a crude product which is used without further purification. LC-MS: tR=0.68 min; [M+H]+=208.0.

Workup

  1. customthe solvents are removed in vacuo
  2. additionWater and DCM are added
  3. customthe layers are separated
  4. washthe organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvents are removed in vacuo

Sources & evidence

ORD record
ord-84b07eefd193462383f41501944ee39c
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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