Dimethylformamide → HCID 86607442, compound

HRID 969503Notes

Reaction equation

HRID 969503 reaction equation
[CH3:1][C:2]1[N:23]([CH3:24])[C:5]2[CH:6]=[C:7]([C:20]([OH:22])=O)[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.[NH:25]1[CH2:27][CH2:26]1.C[N:29](C)C=O>O1CCCC1>[N:25]1([NH:29][C:20]([C:7]2[C:8]3[CH2:9][CH2:10][CH:11]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[NH:12][C:13]=3[C:4]3[N:3]=[C:2]([CH3:1])[N:23]([CH3:24])[C:5]=3[CH:6]=2)=[O:22])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 9033AziridineHCID 69134263HCID 69134263, compound

Product 1

HCID 86607442HCID 86607442, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.47 g (1.5 mmol) 2,3-dimethyl-8-phenyl-6,7,8,9-tetrahydro-3H-imidazo[4,5h]quinoline-5-carboxylic acid in 10 ml tetrahydrofuran and 5 ml N,N-dimethylformamide were added 0.4 g (2.5 mmol) N,N′-carbonyldiimidazole. After 1 h at 60° C., the solution was cooled down and 0.8 g (18.6 mmol) aziridine were added in 4 portions over a period of 3 h. After complete reaction, the organic layer was separated, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (ethyl acetate/light petroleum ether=7:3). Crystallization from diethyl ether/n-heptane yielded 0.23 g (46%) of the title compound as a colourless solid. m.p. 192-193° C.

Workup

  1. temperaturethe solution was cooled down
  2. customAfter complete reaction
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate/light petroleum ether=7:3)
  7. customCrystallization from diethyl ether/n-heptane

Sources & evidence

ORD record
ord-eb19da4f368743fd94b6eb9d95d9f716
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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