Potassium Sodium Tartrate → HCID 23445049, compound

HRID 433634Notes

Reaction equation

HRID 433634 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:11]2[CH:12]=[N:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:10]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C1COCC1.CCOC(C)=O>[N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[C:11]([N:9]2[CH:10]=[C:6]([CH2:4][OH:3])[N:7]=[CH:8]2)[CH:12]=1

Participants

7

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 69037625HCID 69037625, compound

Product 1

HCID 23445049HCID 23445049, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

A suspension of 1-quinolin-3-yl-1H-imidazole-4-carboxylic acid ethyl ester (5.0 g, 18.7 mmol) in toluene (100 ml) was cooled to −78° C. Diisobutylaluminum hydride (19 ml of a 1M solution in THF, 19 mmol) was added dropwise keeping T<−70° C. The mixture was stirred at this temperature for 2 h, then the reaction mixture was allowed to slowly reach 0° C. After addition of saturated aqueous Seignette salt solution (10 ml) stirring was continued for 1 h. The mixture was diluted with AcOEt (100 ml), filtered, concentrated and chromatographed [silica, elution with gradient CH2Cl2 to 80% (CH2Cl2/MeOH/aq. NH4OH=90:10:1)]]. The title compound was obtained as a light-brown crystalline solid (1.20 g, 28%). Mp. 142-145° C. (AcOEt), MS: m/e=226 (M+H+).

Workup

  1. customwas allowed to slowly reach 0° C
  2. stirringstirring
  3. waitwas continued for 1 h
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed
  7. wash[silica, elution with gradient CH2Cl2 to 80% (CH2Cl2/MeOH/aq. NH4OH=90:10:1)]]

Sources & evidence

ORD record
ord-6c68ac1c8fef47159d32f83175ef2723
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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