Sodium Hydroxide → HCID 25192993, compound

HRID 450350Notes

Reaction equation

HRID 450350 reaction equation
[N:1]1[C:10]2[CH:9]([NH2:11])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl[CH2:13][CH2:14][N:15]=[C:16]=[O:17].[OH-].[Na+]>ClCCl.O>[O:17]1[CH2:13][CH2:14][N:15]=[C:16]1[NH:11][CH:9]1[C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 160352-Chloroethyl isocyanateHCID 113555648-Amino-5,6,7,8-tetrahydroquinoline2×

Product 1

HCID 25192993HCID 25192993, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 5,6,7,8-tetrahydroquinolin-8-amine (Intermediate 17) (3.0 mmol) in dichloromethane (10 mL) was added chloroethylisocyanate (3.3 mmol). The solution was stirred at room temperature for 1.5 hour. The solvent was removed under vacuum gave a crude material, which was refluxed in H2O (60 mL) for 1 hour. After cooling to room temperature, the reaction was basified with NaOH (pH 14), extracted in Ethyl acetate (3×50 mL). The pooled organic layers were washed with brine and dried over magnesium sulphate to give 747. (4,5-Dihydro-oxazol-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine, 747 as a solid.

Workup

  1. customThe solvent was removed under vacuum
  2. customgave a crude material, which
  3. temperatureAfter cooling to room temperature
  4. extractionextracted in Ethyl acetate (3×50 mL)
  5. washThe pooled organic layers were washed with brine
  6. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-d0dadf3cb53c4032b8ac95aa8541deb1
Source dataset
uspto-grants-2013_07
Patent number
US08486969B2

Reaction notes

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