2-Amino-3-Hydroxypyridine → HCID 12354095, compound

HRID 1658499Notes

Reaction equation

HRID 1658499 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.CC[O:11][C:12]([CH:14]1[C:18](=O)[CH2:17][CH2:16][CH2:15]1)=O>C(C1C=CC=CC=1CC)C>[OH:8][C:7]1[C:2]2=[N:1][C:15]3[CH2:16][CH2:17][CH2:18][C:14]=3[C:12](=[O:11])[N:3]2[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 281142-Amino-3-HydroxypyridineHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 12354095HCID 12354095, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 86571,2-DiethylbenzeneSolvent

Procedure

A solution of 22.0 g of 2-amino-3-pyridinol, 62.4 g of ethyl cyclopentanone-2-carboxylate, and 200 ml of diethylbenzene is stirred and heated by means of oil bath maintained at ca. 150° for 1 hour, then gradually raised to 195°, and kept at 195° for 1 hour. Some tarry products are formed; hence the diethylbenzene solution is decanted from the tar and the diethylbenzene solution concentrated in vacuo. The residue, 29.8 g is recrystallized from 1400 ml of Skellysolve E to give 22.4 g of product, mp 136°-142°.

Workup

  1. temperatureheated by means of oil bath
  2. temperaturemaintained at ca. 150° for 1 hour
  3. temperaturegradually raised to 195°
  4. customSome tarry products are formed
  5. customhence the diethylbenzene solution is decanted from the tar
  6. concentrationthe diethylbenzene solution concentrated in vacuo
  7. customThe residue, 29.8 g is recrystallized from 1400 ml of Skellysolve E

Sources & evidence

ORD record
ord-00daa38836294651828c1efd10310e17
Source dataset
uspto-grants-1976_06
Patent number
US03965100

Reaction notes

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