Methylamine → HCID 23296648, compound

HRID 1954399Notes

Reaction equation

HRID 1954399 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][C:11]2[CH:20]=[C:19]([CH3:21])[C:18]3[C:13](=[CH:14][C:15]([N:22]4C(=O)C5=CC=CC=C5C4=O)=[CH:16][CH:17]=3)[N:12]=2)=[CH:5][CH:4]=1)#[N:2].CN>C1(C)C=CC=CC=1.CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:9][CH2:10][C:11]2[CH:20]=[C:19]([CH3:21])[C:18]3[C:13](=[CH:14][C:15]([NH2:22])=[CH:16][CH:17]=3)[N:12]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 23296476HCID 23296476, compound

Product 1

HCID 23296648HCID 23296648, compound

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

2.15 g (5.1 mmol) of 2-[(4-cyanophenyl)-oxymethyl]-4-methyl-7-phthalimido-quinoline are dissolved in 75 ml of toluene/methanol (2:1), mixed with 7.5 ml of 40% aqueous methylamine solution and stirred for 2 hours at ambient temperature. Then the solution is concentrated by evaporation in vacuo, the residue is stirred with 2N acetic acid, suction filtered and dried. The crude product is chromatographed on silica gel, eluting first with methylene chloride, later with methylene chloride/ethanol (50:1). The desired fractions are combined, concentrated by evaporation and triturated with ether.

Workup

  1. concentrationThen the solution is concentrated by evaporation in vacuo
  2. stirringthe residue is stirred with 2N acetic acid, suction
  3. filtrationfiltered
  4. customdried
  5. customThe crude product is chromatographed on silica gel
  6. washeluting first with methylene chloride, later with methylene chloride/ethanol (50:1)
  7. concentrationconcentrated by evaporation
  8. customtriturated with ether

Sources & evidence

ORD record
ord-acb9dd0111104cebacd4d94394bfe7cd
Source dataset
uspto-grants-2000_09
Patent number
US06121308

Reaction notes

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