Hydrochloric Acid → (1-Benzylindazol-3-yl)methanol

HRID 1805900Notes

Reaction equation

HRID 1805900 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=[O:18])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][OH:18])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 46934178HCID 46934178, compound

Product 1

HCID 10657568(1-Benzylindazol-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

1-benzyl-1H-indazol-3-carbaldehyde (2.36 g, 10 mmol, 1 eq.) and toluene (12 mL) were placed in a thoroughly dried 100 mL flask fitted with a magnetic stirrer and inerted with nitrogen. A 70% solution of sodium dihydro-bis(2-methoxyethoxy)aluminate in toluene (2.8 mL, 10 mmol, 2 eq.) was then slowly added to the solution at room temperature. Once the reaction was complete (after approximately 15 minutes), 2 M HCl (10 mL), H2O (10 mL) and toluene (15 mL) were added. The phases were separated and the aqueous phase was extracted twice with toluene. The pooled organic phases were washed with water and concentrated. The product was then precipitated out by adding n-hexane, filtered and dried. Yield: 1.95 g of white solid (82.0%).

Workup

  1. customfitted with a magnetic stirrer and inerted with nitrogen
  2. additionwere added
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted twice with toluene
  5. washThe pooled organic phases were washed with water
  6. concentrationconcentrated
  7. customThe product was then precipitated out
  8. additionby adding n-hexane
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-89ac30a36d8c4478ba3207c0bdb7a977
Source dataset
uspto-grants-2013_01
Patent number
US08354544B2

Reaction notes

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