(4-Chlorophenyl)hydrazine → HCID 178515181, compound

HRID 745956Notes

Reaction equation

HRID 745956 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]2[CH2:13][S:14][CH2:15][C:3]=12.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][NH2:24])=[CH:19][CH:18]=1>C(O)CCC>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:8](=[O:10])[C:7]3[C:2]([C:3]4[CH2:15][S:14][CH2:13][C:4]=4[NH:5][CH:6]=3)=[N:24]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 70624(4-Chlorophenyl)hydrazineHCID 13713224HCID 13713224, compound

Product 1

HCID 178515181HCID 178515181, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 0.6 g of ethyl 4-chloro-5,7-dihydrothieno[3,4-b]pyridine-3-carboxylate, p-chlorophenylhydrazine (0.35 g) and 10 ml of n-butanol is heated at reflux for 24 hours, then evaporated to dryness. To the residue is added additional p-chlorophenylhydrazine (0.35 g) and 10 ml of N-methyl-2-pyrrolidone, and the mixture is heated at 150° for 18 hours, then evaporated to dryness. The residue is treated with 20 ml of 2N NaOH and 40 ml of ether. Alkaline layer is separated and pH adjusted to 6.5 depositing solid which is dissolved in methanol; the solution is decolorized with charcoal and concentrated to deposit crystals. Recrystalization from methanol affords 2-(p-chlorophenyl)-2,3,6,8-tetrahydrothieno[3,4-b]pyrazolo[3,4-d]pyridin-3(5H)-one, mp>330°; IR(cm-1)1600, 1570, 1470, 1000, 931, 835, 830 and 762; (the compound of formula IA wherein R1 =p-chlorophenyl, R2 and R3 =H and A represents ##STR26##

Workup

  1. temperatureis heated
  2. temperatureat reflux for 24 hours
  3. customevaporated to dryness
  4. additionTo the residue is added additional p-chlorophenylhydrazine (0.35 g) and 10 ml of N-methyl-2-pyrrolidone
  5. temperaturethe mixture is heated at 150° for 18 hours
  6. customevaporated to dryness
  7. additionThe residue is treated with 20 ml of 2N NaOH and 40 ml of ether
  8. customAlkaline layer is separated
  9. dissolutionis dissolved in methanol
  10. concentrationconcentrated
  11. customRecrystalization from methanol

Sources & evidence

ORD record
ord-bea2f848a49b4c2ab1b2ba954b5a9c85
Source dataset
uspto-grants-1986_07
Patent number
US04602014

Reaction notes

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