Sulfuric Acid → 2-(3-Carbamoylphenyl)acetic acid

HRID 906085Notes

Reaction equation

HRID 906085 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].S(=O)(=O)(O)[OH:14]>FC(F)(F)C(O)=O>[NH2:2][C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1)=[O:14]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 15193972-(3-Cyanophenyl)acetic acid

Product 1

HCID 577487062-(3-Carbamoylphenyl)acetic acidYield 75%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-cyanophenylacetic acid (0.2 g, 1.24 mmol) in a mixture of trifluoroacetic acid (1 ml) and concentrated sulfuric acid (0.5 ml) was stirred at room temperature for 16 h. The reaction mixture was then poured into ice-cold water and the resulting solid was filtered, washed with water and dried under vacuum to give 2-[3-(aminocarbonyl)phenyl]acetic acid (0.167 g, 75% yield). MS (EI) for C9H9NO3: 178 (M−H).

Workup

  1. additionThe reaction mixture was then poured into ice-cold water
  2. filtrationthe resulting solid was filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-5ff80e2dc5f24e4f8547d61a8b4dda9d
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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