Sulfuric Acid → HCID 59164407, compound

HRID 906590Notes

Reaction equation

HRID 906590 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][F:11])=[CH:6][C:5]=1[NH:12]C(=O)C.S(=O)(=O)(O)O>CO>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][F:11])=[CH:6][C:5]=1[NH2:12]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 59164463HCID 59164463, compound

Product 1

HCID 59164407HCID 59164407, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-acetylamino-4-fluoromethyl-benzoic acid methyl ester (1.5 g, 6.66 equiv) in MeOH (50 mL) was added concd sulfuric acid (4 mL) and the mixture was refluxed for 1 h. The mixture was cooled down and concentrated in vacuo. Water was added and the pH was adjusted to 9-10 by addition of 2N NaOH. The aqueous phase was extracted with AcOEt. The organic phase were combined, washed with brine and dried (Na2SO4). The solution was concentrated in vacuo to afford the title compound as a yellow-orange oil (1.24 g, 100%) (ES-MS: m/z 184.1 [M+H]+, rt 4.91 min).

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. temperatureThe mixture was cooled down
  3. concentrationconcentrated in vacuo
  4. additionWater was added
  5. additionthe pH was adjusted to 9-10 by addition of 2N NaOH
  6. extractionThe aqueous phase was extracted with AcOEt
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-91f1810d21744b32a3422afca8d23446
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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