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

HRID 1097055Notes

Reaction equation

HRID 1097055 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:13](=[O:16])(O)[O-].[Na+].[CH2:18](Cl)[CH:19]=C>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:13](=[O:16])[CH:18]=[CH2:19])[CH:5]=1

Participants

5

Reactant 3

HCID 7850Allyl 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-propenyl 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-ca1767cce6e74c7d906aa25e361fb4aa
Source dataset
uspto-grants-2012_03
Patent number
US08138345B2

Reaction notes

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