Ethyl hexanoate → 7-Butyl-8-hydroxy-5-phenylpyrido[2,3-b]pyrazin-6(5H)-one

HRID 1248949Notes

Reaction equation

HRID 1248949 reaction equation
[C:1]1([NH:7][C:8]2[C:13]([C:14]([O:16]C)=O)=[N:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](OCC)(=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].CC(C)([O-])C.[K+]>>[CH2:20]([C:19]1[C:18](=[O:24])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2=[N:9][CH:10]=[CH:11][N:12]=[C:13]2[C:14]=1[OH:16])[CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 3

HCID 31265Ethyl hexanoateHCID 13370930Methyl 3-anilinopyrazine-2-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 546800437-Butyl-8-hydroxy-5-phenylpyrido[2,3-b]pyrazin-6(5H)-one

Procedure

A mixture of 3.5 g. of methyl 2-phenylamino-3pyrazine carboxylate, 30 ml. of ethyl caproate and 4 g. of potassium tertiary butoxide is stirred and heated under nitrogen at 150°-160° for one and a half hours. The reaction mixture is poured on ice, extracted with ethyl acetate and the ethyl acetate extracts washed with water. The combined aqueous layers are acidified to pH 5.5 with dilute hydrochloric acid and the solid filtered. Recrystallization from ethyl acetate-hexane yields the product of this example as a colorless solid; m.p. 183°-185° C.

Workup

  1. additionA mixture of 3.5 g
  2. temperatureheated under nitrogen at 150°-160° for one and a half hours
  3. additionThe reaction mixture is poured on ice
  4. extractionextracted with ethyl acetate
  5. washthe ethyl acetate extracts washed with water
  6. filtrationthe solid filtered
  7. customRecrystallization from ethyl acetate-hexane
  8. customyields the product of this example as a colorless solid

Sources & evidence

ORD record
ord-b339ff4929ad4f67a41eebe92d79b592
Source dataset
uspto-grants-1986_12
Patent number
US04628055

Reaction notes

Loading…