Methyl propiolate → HCID 178492908, compound

HRID 639007Notes

Reaction equation

HRID 639007 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:10].[C:11](OC)(=[O:14])[C:12]#[CH:13]>CO>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]2[C:3]=1[N:10]=[CH:13][CH:12]=[C:11]2[OH:14]

Participants

4

Reactant 2

HCID 13536Methyl propiolateHCID 37563832-Fluoro-4-methoxyaniline

Product 1

HCID 178492908HCID 178492908, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

2-Fluoro-4-methoxyphenylamine (3.80 g, 26.7 mmole) and methyl propiolate (2.37 ml, 0.267 mole) in methanol (100 ml) was stirred for 72 hours at room temperature, then heated at 50° C. for 24 hours. It was evaporated and the product purified by chromatography on silica gel (dichloromethane) to give a solid (1.66 g), a portion of which was recrystallised from dichloromethane-hexane. The unsaturated ester (0.96 g) in warm Dowtherm A (5 ml) was added over 3 minutes to refluxing Dowtherm A (15 ml), and after a further 20 minutes at reflux the mixture was cooled and poured into diethyl ether. The precipate was filtered to give the title compound (0.50 g, 61%). MS (ES) m/e 196 (M+H)+.

Workup

  1. customIt was evaporated
  2. customthe product purified by chromatography on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-d1996cb689ae46339d9f07fbcbd9f051
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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