Sodium hydride → HCID 11574702, compound

HRID 1441938Notes

Reaction equation

HRID 1441938 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]=[C:29]=[O:30]>O1CCCC1>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:29](=[O:30])[NH:28][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[Cl:21])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76833Chlorophenyl isocyanateHCID 68543194HCID 68543194, compound

Product 1

HCID 11574702HCID 11574702, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-ol (0.239 g., 1 mmol) in dry tetrahydrofuran (5 ml) was added to a stirred suspension of sodium hydride (0.024 g, 1 mmol) in dry tetrahydrofuran (5 ml) at −10° C. during 5 min. The reaction mixture was stirred for 20 min. Then 2-chloro-phenyl isocyanate was added (0.184 g., 1.2 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 (34° C.). The reaction mixture was quenched with water (0.2 ml), concentrated under vaccum, diluted with water (5 ml), extracted with chloroform (2×5 ml) and dried over sodium sulphate. The combined fractions of chloroform were concentrated under vaccum. The residue was chromatographed on silica gel using chloroform: hexane (20:80) as eluant to give 2i; yield: 0.20 g. (50.9%), m.p. 130° C., C23H21ClN2O2; 1H NMR δ ppm (CDCl3): 1.90-2.02 (m, 2H), 2.82 (t, 2H), 3.30-3.35 (m, 2H), 4.46 (s, 2H), 6.43-6.48 (m, 1H), 6.74-6.82 (m, 2H), 7.20-7.25 (m, 5H), 7.44-7.46 (m, 4H); IR vmax (KBr) (cm−1): 534, 754, 807, 882, 1018, 1059, 1193, 1245, 1303, 1352, 1432, 1506, 1597, 1718, 1749, 2371, 2830, 2922, 3418, 3760.

Workup

  1. additionwas added to the stirring reaction mixture
  2. stirringStirring
  3. waitwas continued for additional 2.5 hours during which
  4. customto rise to room temperature
  5. custom(34° C.)
  6. customThe reaction mixture was quenched with water (0.2 ml)
  7. concentrationconcentrated under vaccum
  8. additiondiluted with water (5 ml)
  9. extractionextracted with chloroform (2×5 ml)
  10. dry with materialdried over sodium sulphate
  11. concentrationThe combined fractions of chloroform were concentrated under vaccum
  12. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-b440d446665f40f6a4e1c1ef3713d942
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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