Ethanol → [2-(3-Aminoprop-1-yn-1-yl)-5-chlorophenyl](2-fluorophenyl)methanone

HRID 464592Notes

Reaction equation

HRID 464592 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][N:11]2C(=O)C3=CC=CC=C3C2=O)=[C:4]([C:22](=[O:30])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])[CH:3]=1.C(O)C.CN>O>[NH2:11][CH2:10][C:9]#[C:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[C:22](=[O:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[F:29]

Participants

5

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 12878253HCID 12878253, compound

Product 1

HCID 12948270[2-(3-Aminoprop-1-yn-1-yl)-5-chlorophenyl](2-fluorophenyl)methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Method B A mixture of 400 g (0.96 mole) of 1-[4-chloro-2-(2-fluorobenzoyl)phenyl]-3-phthalimidopropyne, 1.3 L of ethanol and 300 ml of 40% aqueous methylamine was stirred at room temperature for 2 hr. Dropwise 2.8 l of water was added, and the resulting precipitate was collected by filtration to give a pale yellow solid, mp 70°-80° C. Recrystallization from ether gave pale yellow prisms, mp 80°-91° C.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customto give a pale yellow solid, mp 70°-80° C
  3. customRecrystallization from ether
  4. customgave pale yellow prisms, mp 80°-91° C.

Sources & evidence

ORD record
ord-d4ff219e54044bd7a49c0258c4e75ddc
Source dataset
uspto-grants-1985_10
Patent number
US04548750

Reaction notes

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