Acryloyl chloride → 3-(Acryloylmethylamino)benzoic Acid Methyl Ester

HRID 2412281Notes

Reaction equation

HRID 2412281 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH3:11])[CH:5]=1.C(=O)(O)[O-].[Na+].[C:18](Cl)(=[O:21])[CH:19]=[CH2:20]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH2:11][C:18](=[O:21])[CH:19]=[CH2:20])[CH:5]=1

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 516892Sodium Bicarbonate2×HCID 10899041Benzoic acid, 3-(methylamino)-, methyl ester

Product 1

HCID 667703313-(Acryloylmethylamino)benzoic Acid Methyl EsterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 3-methylaminobenzoic acid methyl ester (3.11 g, 18.8 mmol) and sodium bicarbonate (3.16 g, 37.6 mmol) in DCM (20.0 mL) at 0° C. was added 2-propenoyl chloride (2.29 mL, 28.2 mmol). The reaction mixture was stirred overnight at room temperature. Saturated aqueous sodium bicarbonate solution was added and the layers were separated. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (4.12 g, 100% yield), which was used in the next reaction without further purification.

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4973292cce94b83a62f8e09b6c3332c
Source dataset
uspto-grants-2014_08
Patent number
US08816088B2

Reaction notes

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