Hydrochloric Acid → HCID 15319941, compound

HRID 366384Notes

Reaction equation

HRID 366384 reaction equation
O[CH2:2][C:3]1[C:4](=O)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][NH2:22])=[CH:17][CH:16]=1.Cl>C(O)C>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:11]3[C:10]4[C:5]([CH2:4][C:3]=3[CH:2]=[N:22]2)=[CH:6][CH:7]=[CH:8][CH:9]=4)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 23289834HCID 23289834, compound

Product 1

HCID 15319941HCID 15319941, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hydroxymethyl inden-1-one (Example 1(ii)(a) (4.0 g; 25.00 mmol), p-chlorophenylhydrazine hydrochloride (Aldrich) (4.52 g; 25.25 mmol), 10M hydrochloric acid (1 cm3) and ethanol (30 cm3) were heated under reflux for 22 hours. After cooling, the solvent was evaporated and the residual dissolved in dichloromethane and washed with 2M sodium hydroxide. The organic extracts were then dried (Na2SO4), filtered and concentrated in vacuo. Purification was by column chromatography (Eluant: dichloromethane] and recrystallisation (ethanol) gave off-white needle shaped crystals, m.p. 128-129° C.; b.p. 185° C.; 0.05 mmHg.

Workup

  1. temperatureunder reflux for 22 hours
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. dissolutionthe residual dissolved in dichloromethane
  5. washwashed with 2M sodium hydroxide
  6. dry with materialThe organic extracts were then dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification
  10. customdichloromethane] and recrystallisation (ethanol)
  11. customgave off-white needle

Sources & evidence

ORD record
ord-cd7d6171e23244dcb256c55d360c2f09
Source dataset
uspto-grants-2000_10
Patent number
US06130228

Reaction notes

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