Acetic Anhydride → HCID 54287785, compound

HRID 2188463Notes

Reaction equation

HRID 2188463 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[N:12]1[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=1.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[CH:18][C:15]2[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=2)[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 98372-(4-Fluorophenyl)acetic acidHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 54287785HCID 54287785, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-fluorophenylacetic acid (9 g, 58.4 mmol), 4-pyridinecarboxaldehyde (5.6 ml, 58.6 mmol), pyridine (6 ml) and acetic anhydride (6 ml) was heated at 150° C. for 1 h followed by evaporation and co-distillation with water. The resulting material crystallized on addition of ethanol. The solids were filtered and washed with ethanol and ethyl acetate to provide the title compound. MS (m/z): 244.0 (M+H)+; C14H10FNO2requir. 243.2 1H-NMR (DMSO-d6): d 8.43, 6.98 (2d, each 2H, Pyrid.), 7.73 (s, 1H, CH═), 7.21 (d, 4H, PhF).

Workup

  1. customfollowed by evaporation and co-distillation with water
  2. customThe resulting material crystallized on addition of ethanol
  3. filtrationThe solids were filtered
  4. washwashed with ethanol and ethyl acetate

Sources & evidence

ORD record
ord-361d0a76f5a94fce952c723dbb4e8e4c
Source dataset
uspto-grants-2002_06
Patent number
US06410729B1

Reaction notes

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