Water → HCID 69135081, compound

HRID 969502Notes

Reaction equation

HRID 969502 reaction equation
[CH3:1][C:2]1[N:23]([CH3:24])[C:5]2[CH:6]=[C:7]([C:20](O)=[O:21])[C:8]3[CH2:9][CH2:10][CH:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:12][C:13]=3[C:4]=2[N:3]=1.[CH3:25][NH2:26].O>O1CCCC1.CN(C)C=O>[CH3:25][NH:26][C:20]([C:7]1[C:8]2[CH2:9][CH2:10][CH:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:12][C:13]=2[C:4]2[N:3]=[C:2]([CH3:1])[N:23]([CH3:24])[C:5]=2[CH:6]=1)=[O:21]

Participants

6

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 69134263HCID 69134263, compound

Product 1

HCID 69135081HCID 69135081, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1.0 g (3.1 mmol) 2,3-dimethyl-8-phenyl-6,7,8,9-tetrahydro-3H-imidazo[4,5-h]quinoline-5-carboxylic acid in 10 ml tetrahydrofuran and 5 ml N,N-dimethylformamide were added 1.0 g (6.2 mmol) N,N′-carbonyldiimidazole. After 1 h at 60° C., the solution was cooled down and 15.6 ml (31.2 mmol) methylamine (2M in tetrahydrofuran) were added. The mixture was stirred 2 h at ambient temperature and then poured into 50 ml water. The precipitate was collected, washed with water and dried at 50° C. to yield 0.87 g (84%) of the title compound. m.p. 259° C.

Workup

  1. temperaturethe solution was cooled down
  2. customThe precipitate was collected
  3. washwashed with water
  4. customdried at 50° C.

Sources & evidence

ORD record
ord-ad94c8060de54ce5976e86759dc0f99a
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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