Sodium Hydroxide → HCID 15053193, compound

HRID 1088827Notes

Reaction equation

HRID 1088827 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8]=1[S:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:27]=1[N:26]([CH2:28][CH3:29])[CH2:25][CH:24]([C:30](OCC)=[O:31])[CH2:23]2.[OH-].[Na+]>O1CCCC1.O>[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8]=1[S:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:27]=1[N:26]([CH2:28][CH3:29])[CH2:25][CH:24]([CH2:30][OH:31])[CH2:23]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22161804HCID 22161804, compound

Product 1

HCID 15053193HCID 15053193, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminium hydride (0.3 g) in tetrahydrofuran (50 ml) was added dropwise a solution of 8-(2-benzimidazolyl)thiomethyl-1-ethyl-3-ethoxycarbonyl-1,2,3,4-tetrahydroquinoline (1.0 g) in tetrahydrofuran (10 ml) with stirring under ice-cooling. The mixture was stirred for 3 hours at the same temperature. To the reaction mixture were added water (0.3 ml) and a solution of sodium hydroxide (0.3 g) in water (1.5 ml). After filtering off the precipitate, the filtrate was dried over anhydrous magnesium sulfate. After distilling off tetrahydrofuran, the resulting residue was recrystallized from ethanol to give 8-(2-benzimidazolyl)thiomethyl-1-ethyl-3-hydroxymethyl-1,2,3,4-tetrahydroquinoline (0.7 g).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 3 hours at the same temperature
  3. filtrationAfter filtering off the precipitate
  4. dry with materialthe filtrate was dried over anhydrous magnesium sulfate
  5. distillationAfter distilling off tetrahydrofuran
  6. customthe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-254f375cff2849008ccab93dd1b04de4
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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