Sodium hydride → HCID 11709470, compound

HRID 1441947Notes

Reaction equation

HRID 1441947 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[H-].[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]=[C:23]=[O:24]>CN(C)C=O>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:23](=[O:24])[NH:22][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[Cl:15])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76833Chlorophenyl isocyanateHCID 22755149HCID 22755149, compound

Product 1

HCID 11709470HCID 11709470, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1-methyl-1, 2, 3, 4-tetrahydro-quinolin-6-ol (0.326 g., 2 mmol) in dry dimethylformamide (5 ml) was added to a stirred suspension of sodium hydride (0.048 g., 2 mmol) in dry dimethylformamide (5 ml) at −10° C. during 5 min. The reaction mixture was stirred for 30 min. Then 2-chloro-phenyl isocyanate (0.329 g., 2 mmol) was added to the stirring reaction mixture. Stirring was continued for additional 2.5 hours during which the temperature was allowed to rise to room temperature (35° C.). The reaction mixture was quenched with water (0.2 ml), diluted with water (5 ml), extracted with ethyl acetate (2×5 ml) and dried over sodium sulphate. The combined fractions of ethyl acetate were concentrated under vaccum. The residue was chromatographed on silica gel using chloroform: hexane (20:80) as eluant to give 2o; yield: 0.50 g. (78.9%), m p. 120° C., C17H17ClN2O2; 1H NMR δ ppm (CDCl3); 1.95-2.01 (m, 2H), 2.77 (t, 2H), 2.88 (s, 3H), 3.21 (t, 2H), 6.54-6.58 (m, 1H), 6.81-7.05 (m, 31), 7.23-7.44 (m, 2H), 8.18-8.22 (m, 1H); IR vmax (KBr) (cm−1); 563, 670, 758, 1017, 1201, 1305, 1432, 1507, 1596, 1746, 2375, 2940, 3020, 3282, 3413, 3686, 3763.

Workup

  1. stirringStirring
  2. waitwas continued for additional 2.5 hours during which
  3. customto rise to room temperature
  4. custom(35° C.)
  5. customThe reaction mixture was quenched with water (0.2 ml)
  6. additiondiluted with water (5 ml)
  7. extractionextracted with ethyl acetate (2×5 ml)
  8. dry with materialdried over sodium sulphate
  9. concentrationThe combined fractions of ethyl acetate were concentrated under vaccum
  10. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-31c2e2656f1441ddb5bc4c99c9754f5d
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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