4-Amino-3-hydroxypyridine → 4-[[(1-Piperidinyl)methylene]amino]-3-pyridinol

HRID 361327

Reaction equation

HRID 361327 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[OH:8].CO[C:11](OC)([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)N>>[N:13]1([CH:11]=[N:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[OH:8])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 27624194-Amino-3-hydroxypyridineHCID 570644181-Piperidinylformamide dimethyl acetal

Product 1

HCID 153809334-[[(1-Piperidinyl)methylene]amino]-3-pyridinol

Conditions

Temperature
100 °C

Procedure

4-Amino-3-pyridinol (3.3 g) was added to 1-piperidinylformamide dimethyl acetal (50 ml) and the mixture was stirred at 100° C. until it became homogeneous (approximately one minute). The reaction mixture was cooled, and placed in an ice bath for a half hour. The crystallized product was filtered, washed well with diethyl ether, and air dried to yield 4.64 g of product. This was recrystallized from ethyl acetate and dried under high vacuum and refluxing ethanol overnight to yield 3.39 g of fluffy needles, m.p. 171°-172.5° C.

Workup

  1. custom(approximately one minute)
  2. temperatureThe reaction mixture was cooled
  3. waitplaced in an ice bath for a half hour
  4. filtrationThe crystallized product was filtered
  5. washwashed well with diethyl ether, and air
  6. customdried

Sources & evidence

ORD record
ord-d2979447f54640189cffabeb4a769559
Source dataset
uspto-grants-1999_02
Patent number
US05866565

Linked notes

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