Dimethylformamide → HCID 69135053, compound

HRID 969501Notes

Reaction equation

HRID 969501 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.C[N:26](C)C=O>O1CCCC1>[CH3:1][C:2]1[N:23]([CH3:24])[C:5]2[CH:6]=[C:7]([C:20]([NH2:26])=[O:22])[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

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 69134263HCID 69134263, compound

Product 1

HCID 69135053HCID 69135053, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.9 g (2.8 mmol) 2,3-dimethyl-8-phenyl-6,7,8,9-tetrahydro-3H-imidazo[4,5h]quinoline-5-carboxylic acid in 10 ml tetrahydrofuran and 8 ml N,N-dimethylformamide were added 0.5 g (3.1 mmol) N,N′-carbonyldiimidazole. After 4 h at 60° C., the solution was cooled down and ammonia was bubbled through the flask for 4 h. The mixture was allowed to stand 60 h and then poured into 100 ml water. The precipitate was collected, washed with water and dried at 50° C. to yield 0.64 g (71%) of the title compound. m.p. 311-319° C.

Workup

  1. temperaturethe solution was cooled down
  2. customammonia was bubbled through the flask for 4 h
  3. waitto stand 60 h
  4. additionpoured into 100 ml water
  5. customThe precipitate was collected
  6. washwashed with water
  7. customdried at 50° C.

Sources & evidence

ORD record
ord-9a68077fa3154c73a3a26b41112eac47
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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