Hydrochloric Acid → HCID 15512311, compound

HRID 2258464Notes

Reaction equation

HRID 2258464 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1)[N:7]=[C:6]2[C:25]([O-])=[O:26].[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>O1CCCC1.O.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1)[N:7]=[C:6]2[CH2:25][OH:26]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride2×HCID 18938889HCID 18938889, compound

Product 1

HCID 15512311HCID 15512311, compoundYield 93.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5,6-Dimethoxy-l-(3,4-dimethoxybenzyl)-1H-indazole-3-carboxylate (205.0 g) was ground in a mortar and suspended in tetrahydrofuran (1500 ml) at room temperature. Then sodium borohydride (96.8 g) was added thereto and the mixture was stirred at room temperature. Methanol (300 ml) was slowly added dropwise thereinto within 30 minutes. After the completion of the addition, the reaction mixture was heated to 50° C. and stirred for 5 hours. After adding sodium borohydride (19.4 g) and methanol (60 ml), the mixture was stirred at room temperature overnight. Then the reaction mixture was added in portions into a mixture of conc. hydrochloric acid (200 ml), water (5000 ml) and ice (1 kg) under stirring (pH 1-2). To this aqueous layer, a saturated aqueous solution of sodium bicarbonate was added with stirring at room temperature until the pH became about 8. As a result, a colorless solid was precipitated. This precipitate was collected by filtration, washed with water (500 ml×2), dissolved in chloroform (10000 ml), dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. Thus a colorless solid (185.2 g) was obtained. This solid product was used in the subsequent reaction without purification.

Workup

  1. additionAfter the completion of the addition
  2. temperaturethe reaction mixture was heated to 50° C.
  3. stirringstirred for 5 hours
  4. stirringthe mixture was stirred at room temperature overnight
  5. stirringunder stirring (pH 1-2)
  6. stirringwith stirring at room temperature until the pH
  7. customAs a result, a colorless solid was precipitated
  8. filtrationThis precipitate was collected by filtration
  9. washwashed with water (500 ml×2)
  10. dissolutiondissolved in chloroform (10000 ml)
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b24252a52ba84d028b3f71cf0c79f9f9
Source dataset
uspto-grants-1997_08
Patent number
US05661150

Reaction notes

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