Hydrazine → HCID 178418907, compound

HRID 9287

Reaction equation

HRID 9287 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH:7]2[CH2:16][CH2:15][C:14]3[N:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:8]2=O)[N:3]=[CH:2]1.NN.[OH-].[K+]>C(O)COCCO.O.C([O-])(O)=O.[Na+]>[NH:1]1[CH:5]=[C:4]([CH2:6][CH:7]2[CH2:16][CH2:15][C:14]3[N:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH2:8]2)[N:3]=[CH:2]1

Participants

7

Reactant 3

HCID 9321HydrazineHCID 14797Potassium HydroxideHCID 178418911HCID 178418911, compound

Product 1

HCID 178418907HCID 178418907, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8117Diethylene GlycolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
170 °C

Procedure

Use of 7,8-dihydro-6H-quinolin-5-one (Intermediate TWENTYTWO-1) (obtained as described in Molina, et. al. Tetrahedron 1995, 51, 1265, incorporated herein by reference) in Method E produced 6-(1H-imidazol-4-ylmethyl)-7,8-dihydro-6H-quinolin-5-one (Intermediate TWENTYTWO-2). To a solution of 6-(1H-imidazol-4-ylmethyl)-7,8-dihydro-6H-quinolin-5-one (Intermediate TWENTYTWO-2) (1.31 g, 227 mmol) in diethylene glycol (10 mL) was added hydrazine (6.3 mL, 200 mmol) followed by KOH (4.85 g, 56.2 mmol). The mixture was heated to 170° C. for 5 h. The mixture was diluted with water (200 mL) and sat. NaHCO3. The aqueous solution was extracted with CHCl3 (3×50 mL). The combined organic portions were washed with water and brine. The organic layer was dried over MgSO4, filtered and evaporated to give 6-(1H-imidazol-4-ylmethyl)-5,6,7,8-tetrahydro-quinoline as a foamy solid, 1.15 g (92%). By the applicable process steps described in Method A, the imidazole compound was used to produce 4-(5,6,7,8-tetrahydro-quinolin-6-ylmethyl)-1,3-dihydro-imidazole-2-thione (Compound 162).

Workup

  1. extractionThe aqueous solution was extracted with CHCl3 (3×50 mL)
  2. washThe combined organic portions were washed with water and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9b9de1057bbe403baed0bb47fffa7c28
Source dataset
uspto-grants-2006_08
Patent number
US07091232B2

Linked notes

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