Hydrochloric Acid → HCID 53682417, compound

HRID 842604Notes

Reaction equation

HRID 842604 reaction equation
[BH4-].[Na+].[C:3]([NH:6][C:7]1[C:14]([OH:15])=[C:13]([O:16][CH3:17])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10])(=[O:5])[CH3:4].Cl>CO>[C:3]([NH:6][C:7]1[C:14]([OH:15])=[C:13]([O:16][CH3:17])[CH:12]=[CH:11][C:8]=1[CH2:9][OH:10])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22614793HCID 22614793, compound

Product 1

HCID 53682417HCID 53682417, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (550 mg, 14.53 mmol) is slowly added to a solution of 2-acetamido-3-hydroxy-4-methoxybenzaldehyde (3.0 g, 14.34 mmol) [M. Grossa, F. Wessely Monatsh. Chem. 1966, 97, 1384-1390] in methanol (80 ml). After stirring for 10 minutes, the suspension is poured onto a 0.1 N aqueous HCl solution (50 ml) and then extracted with CH2Cl2 (3 times). The organic phases are combined, dried over MgSO4, filtered off and concentrated in vacuo. The residue obtained is purified by means of chromatography with pure ethyl acetate and yields the title compound as a colorless solid (2.2 g). TLC, silica gel (glass plates), ethyl acetate, Rf=0.19.

Workup

  1. extractionextracted with CH2Cl2 (3 times)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered off
  4. concentrationconcentrated in vacuo
  5. customThe residue obtained
  6. customis purified by means of chromatography with pure ethyl acetate

Sources & evidence

ORD record
ord-0ddd8ee20f404f9988c1935b1e084e1a
Source dataset
uspto-grants-2002_04
Patent number
US06376485B1

Reaction notes

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