Pyridine → HCID 11587138, compound

HRID 1441923Notes

Reaction equation

HRID 1441923 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:12]([N:18]=[C:19]=[O:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].N1C=CC=CC=1>CN(C)C=O.O>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:19](=[O:20])[NH:18][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 113746-HydroxyquinolineHCID 75659Hexyl isocyanate

Product 1

HCID 11587138HCID 11587138, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Mixture of quinolin-6-ol (0.58 g., 4 mmol), hexyl isocyanate (0.70 ml, 4.8 mmol) and dry pyridine (0.2 ml) in dry dimethylformamide (1 ml) was heated at 50° C. for 5 hours. Reaction mixture was diluted with water (5 ml), extracted with ethyl acetate (2×5 ml) and dried over sodium sulphate. The combined ethyl acetate fractions were concentrated under vaccum and crystallized with ether to give 1a; yield: 0.7 g. (59.7%).

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate (2×5 ml)
  3. dry with materialdried over sodium sulphate
  4. concentrationThe combined ethyl acetate fractions were concentrated under vaccum
  5. customcrystallized with ether

Sources & evidence

ORD record
ord-e38559ea92694832be018ab3f365ffe7
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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