Acetyl chloride → HCID 59164513, compound

HRID 906588Notes

Reaction equation

HRID 906588 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][C:5]=1[NH2:12].[C:14](Cl)(=[O:16])[CH3:15]>O1CCOCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][C:5]=1[NH:12][C:14](=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 602338Methyl 2-amino-4-(hydroxymethyl)benzoate

Product 1

HCID 59164513HCID 59164513, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-amino-4-hydroxymethyl-benzoic acid methyl ester (7.8 g, 43 mmol) in dioxane (150 mL) was added acetyl chloride (3.04 mL, 1 equiv) and the resulting mixture was stirred at 90° C. for 18 h. The solution was concentrated in vacuo and the resulting oil was sonicated in DCM/hexanes (2/8). The solid was filtered off, washed with hexanes and dried to afford a white solid (7.03 g, 73.2%) (ES-MS: m/z 224.2 [M+H]+, rt 3.75 min).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe resulting oil was sonicated in DCM/hexanes (2/8)
  3. filtrationThe solid was filtered off
  4. washwashed with hexanes
  5. customdried

Sources & evidence

ORD record
ord-7da5e30b59764c10942904576c8e6242
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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