Acetic Anhydride → HCID 54533204, compound

HRID 745754Notes

Reaction equation

HRID 745754 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[CH2:17][C:18]([OH:20])=[O:19].C(N(CC)CC)C.C(OC(=O)C)(=O)C>O>[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[C:17](=[CH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:18]([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 103713-PyridinecarboxaldehydeHCID 882092,4-Dichlorophenylacetic acid

Product 1

HCID 54533204HCID 54533204, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of pyridine-3-aldehyde (21.4 g), 2,4-dichlorophenylacetic acid (40.1 g), triethylamine (20 ml) and acetic anhydride (160 ml) was stirred and heated under reflux for 5 hours while maintaining a temperature of 150° C. After cooling, the reaction mixture was diluted with water (150 ml) and left to stand overnight. The crystalline solid that had separated was filtered off, washed thoroughly with water and dried. After recrystallization from ethanol (600 ml) 1 was obtained as pale yellow crystals; melting point 208-211° C.; yield 71%. The following elemental analysis results were obtained:

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. waitleft
  5. customThe crystalline solid that had separated
  6. filtrationwas filtered off
  7. washwashed thoroughly with water
  8. customdried
  9. customAfter recrystallization from ethanol (600 ml) 1
  10. customwas obtained as pale yellow crystals
  11. customThe following elemental analysis results
  12. customwere obtained

Sources & evidence

ORD record
ord-b5e0ddfef188423198da7b1302851efa
Source dataset
uspto-grants-1986_07
Patent number
US04600712

Reaction notes

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