Allylamine → HCID 11358963, compound

HRID 639891Notes

Reaction equation

HRID 639891 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([C:20]#[N:21])[N:3]=1.[CH2:22]([NH2:25])[CH:23]=[CH2:24]>C(O)CCC>[CH2:22]([NH:25][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([C:20]#[N:21])[N:3]=1)[CH:23]=[CH2:24]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 114264141-Chloro-6-methoxy-4-phenylisoquinoline-3-carbonitrile

Product 1

HCID 11358963HCID 11358963, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a suspension of 104 mg of 1-chloro-6-methoxy-4-phenylisoquinoline-3-carbonitrile in nBuOH was added 252 uL of allylamine. The reaction was heated at 210 C in a microwave reactor for 1 h, then partitioned between EA and saturated aqueous sodium bicarbonate. The organic solution was washed with brine once, then dried (Na2SO4) and concentrated. Flash chromatography (540% EA/hex, Gilson, 40 g silica) gave a pink solid.

Workup

  1. temperatureThe reaction was heated at 210 C in a microwave reactor for 1 h
  2. custompartitioned between EA and saturated aqueous sodium bicarbonate
  3. washThe organic solution was washed with brine once
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customFlash chromatography (540% EA/hex, Gilson, 40 g silica) gave a pink solid

Sources & evidence

ORD record
ord-da367689e4f346b0acee7b07dccadacd
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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