Hydrochloric Acid → HCID 10474189, compound

HRID 1793823Notes

Reaction equation

HRID 1793823 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[CH:18]=[C:17]([OH:19])[C:16]([O:20][CH3:21])=[CH:15][C:14]=2[CH:22]([CH2:26][CH3:27])[C:23](=O)[CH3:24])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH2:28][NH2:29].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:13]3[CH:18]=[C:17]([OH:19])[C:16]([O:20][CH3:21])=[CH:15][C:14]=3[CH:22]([CH2:26][CH3:27])[C:23]([CH3:24])=[N:29][N:28]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 222197323-[2-(3,4-Dimethoxybenzoyl)-4-hydroxy-5-methoxyphenyl]pentan-2-one

Product 1

HCID 10474189HCID 10474189, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 14 g of 3-{2-[(3,4-dimethoxyphenyl)carbonyl]-4-hydroxy-5-methoxyphenyl}pentan-2-one and 4.7 mL of hydrazine in 280 mL of ethanol was heated at reflux for 0.5 hr. After allowing the solution to cool to room temperature, it was saturated with HCl gas. The mixture was then concentrated to a volume of about 5 mL, basified with concentrated ammonium hydroxide, and extracted with methylene chloride. The combined methylene chloride extracts were dried and concentrated, and the residue recrystallized from ethyl acetate/hexane. Yield: 1.5 g

Workup

  1. temperatureat reflux for 0.5 hr
  2. concentrationThe mixture was then concentrated to a volume of about 5 mL
  3. extractionextracted with methylene chloride
  4. dry with materialThe combined methylene chloride extracts were dried
  5. concentrationconcentrated
  6. customthe residue recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-cf908bae29b7404681d8111d8162a2a9
Source dataset
uspto-grants-2006_04
Patent number
US07022700B2

Reaction notes

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