3-Cyanopyridine → HCID 12257652, compound

HRID 1658085Notes

Reaction equation

HRID 1658085 reaction equation
[Na].[C:2]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)#[N:3].C(O)(=O)C.N[C:15]1[CH:16]=[C:17]([CH:22]([CH3:26])[C:23]([OH:25])=[O:24])[CH:18]=[CH:19][C:20]=1[OH:21]>CO.O>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:2]2[O:21][C:20]3[CH:19]=[CH:18][C:17]([CH:22]([CH3:26])[C:23]([OH:25])=[O:24])=[CH:16][C:15]=3[N:3]=2)[CH:5]=1

Participants

7

Reactant 4

HCID 793-CyanopyridineHCID 176Acetic AcidHCID 5360545SodiumHCID 12202637HCID 12202637, compound

Product 1

HCID 12257652HCID 12257652, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium (0.115 g.) was dissolved carefully in methanol (45 ml.) and 3-cyanopyridine (5.2 g.) was added. Next day, acetic acid (0.3 g.) was added followed by 2-(3-amino-4-hydroxyphenyl)propionic acid (9.05 g.). The stirred mixture was heated under reflux for 5 hours. The solid dissolved completely during this time. An equal volume of water was added to the hot solution. On cooling, cream crystals separated which were filtered off and re-crystallised from dimethylformamide-ethanol to yield the desired acid, m.p. 197°- 200°C.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux for 5 hours
  3. dissolutionThe solid dissolved completely during this time
  4. temperatureOn cooling
  5. customcream crystals separated which
  6. filtrationwere filtered off
  7. customre-crystallised from dimethylformamide-ethanol

Sources & evidence

ORD record
ord-60f3f445b85e49588c2aa8b7f2cee1cd
Source dataset
uspto-grants-1976_06
Patent number
US03962441

Reaction notes

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