Hydrochloric Acid → HCID 59691669, compound

HRID 898527Notes

Reaction equation

HRID 898527 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]#[C:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>CCO.[Fe]>[Cl:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[C:12]#[C:13][CH2:14][N:15]([CH2:16][CH3:17])[CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 68875558HCID 68875558, compound

Product 1

HCID 59691669HCID 59691669, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 15 mL of conc. aqueous HCl in 15 mL EtOH was added to a suspension of 4.189 g (75.00 mmol) of iron powder and 2.00 g (7.50 mmol) of [3-(2-chloro-4-nitro-phenyl)-prop-2-ynyl]-diethyl-amine in 20 mL of EtOH with vigorous stirring and the mixture was stirred for 30 minutes. The reaction mixture was neutralised with 200 mL of 10% aqueous sodium carbonate solution and exhaustively extracted with EtOAc. The combined org. phases were dried over magnesium sulphate, evaporated down i. vac. and the residue was purified by column chromatography (silica gel, gradient dichloromethane /10% conc. aqueous ammonia in MeOH 100:0→5:95).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionexhaustively extracted with EtOAc
  3. dry with materialphases were dried over magnesium sulphate
  4. customevaporated down i
  5. customand the residue was purified by column chromatography (silica gel, gradient dichloromethane /10% conc. aqueous ammonia in MeOH 100:0→5:95)

Sources & evidence

ORD record
ord-d4095f7f4ac447f58adbb3e417930d5c
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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