(4-Chlorophenyl)hydrazine → HCID 178515181, compound

HRID 1905687Notes

Reaction equation

HRID 1905687 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 ##STR27## The starting material is prepared as follows:

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-6eafc95fa3ce4f148785620a1d8bb188
Source dataset
uspto-grants-1987_03
Patent number
US04647566

Reaction notes

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