Potassium Hydroxide → HCID 69135162, compound

HRID 969504Notes

Reaction equation

HRID 969504 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[N:31]([CH3:32])[C:11]2[CH:12]=[C:13]([C:26](OCC)=[O:27])[C:14]3[CH2:15][CH2:16][CH:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[NH:18][C:19]=3[C:10]=2[N:9]=1.[OH-].[K+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[OH:27][CH2:26][C:13]1[C:14]2[CH2:15][CH2:16][CH:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:18][C:19]=2[C:10]2[N:9]=[C:8]([CH3:7])[N:31]([CH3:32])[C:11]=2[CH:12]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 69134270HCID 69134270, compound

Product 1

HCID 69135162HCID 69135162, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.2 g (5.3 mmol) lithium aluminium hydride in 15 ml tetrahydrofuran was slowly added a solution of 1.0 g (2.9 mmol) ethyl 2,3-dimethyl-8-phenyl-6,7,8,9-tetrahydro-3H-imidazo[4,5-h]quinoline-5-carboxylate in 5 ml tetrahydrofuran. After 2 h, the reaction mixture was carefully hydrolyzed with 0.1 ml water, 0.2 ml 6N aqueous potassium hydroxide and 0.1 ml water. Anhydrous magnesium sulfate was added and the mixture was stirred 1 h. After filtration through celite, the filtrate was evaporated and the residue purified by column chromatography on silica gel (dichloromethane/methanol=13:1). Crystallization from acetone yielded 0.28 g (32%) of the title compound as a colourness solid. m.p. 253-254° C.

Workup

  1. filtrationAfter filtration through celite
  2. customthe filtrate was evaporated
  3. customthe residue purified by column chromatography on silica gel (dichloromethane/methanol=13:1)
  4. customCrystallization from acetone

Sources & evidence

ORD record
ord-dde4b7d8b1f44dde97f97b9b9ecc871e
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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