Chloroacetyl chloride → HCID 59153381, compound

HRID 560276Notes

Reaction equation

HRID 560276 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]([OH:15])[C:10]=1[NH2:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:6][O:7][C:8]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]2[O:15][CH2:2][C:3](=[O:4])[NH:16][C:10]=12)=[O:17]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 205248Anthranilic acid, 3-hydroxy-, methyl ester

Product 1

HCID 59153381HCID 59153381, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At RT chloro-acetyl chloride (8.06 mmol) is added dropwise to a solution of 2-amino-3-hydroxy-benzoic acid methyl ester (7.33 mmol) in DMF (50 mL). After 20 min K2CO3 (34.9 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 purified by FC (heptane to heptane/EtOAc 6/4). LC-MS: tR=0.82 min; [M+CH3CN+H]+=249.0.

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-ed604b9018c042198d2c4c7dac038dff
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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