Ammonia → Carbon Dioxide

HRID 980841Notes

Reaction equation

HRID 980841 reaction equation
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][C:4]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[C:17](=O)[C:18]([OH:20])=[O:19])=O)=[CH:3][CH:2]=1.[NH3:28]>C(O)C>[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:28]=[C:17]([C:18]([OH:20])=[O:19])[C:11]3[C:10](=[CH:15][CH:14]=[C:13]([F:16])[CH:12]=3)[N:9]=2)=[CH:3][CH:2]=1.[C:18](=[O:20])=[O:19]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 13771995HCID 13771995, compound

Product 2

HCID 280Carbon DioxideHCID 13771996HCID 13771996, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 6 g of 2-[(1,1'-biphenyl-4-yl)carbonylamino]-5-fluoro-α-oxobenzeneacetic acid in ethanol (120 ml) was added anhydrous ammonia (27 g). The resulting mixture was heated in a sealed tube under autogenous conditions at 120° for six hours. The reaction mixture was cooled and the solvent and ammonia removed by evaporation in vacuo. The dry residue was suspended in water (200 ml) and the mixture was acidified with acetic acid to pH 3-4. The precipitated solids were collected, washed thoroughly with water and air dried. Recrystallization from ethanol afforded the title compound, m.p. 168°-169° (dec. with evolution of CO2). Mass. Calcd. for C21H13FN2O2 : 344, found 344.

Workup

  1. temperatureThe resulting mixture was heated in a sealed tube under autogenous conditions at 120° for six hours
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent and ammonia removed by evaporation in vacuo
  4. customThe precipitated solids were collected
  5. washwashed thoroughly with water and air
  6. customdried
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-f1ca4b0ddc4e4685b754b53ca31288e1
Source dataset
uspto-grants-1987_01
Patent number
US04639454

Reaction notes

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