Aminoacetaldehyde dimethyl acetal → HCID 22226486, compound

HRID 900704Notes

Reaction equation

HRID 900704 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH:7]=O)[CH3:2].[CH3:14][O:15][CH:16]([O:19][CH3:20])[CH2:17][NH2:18].[BH4-].[Na+]>C(O)C>[CH3:14][O:15][CH:16]([O:19][CH3:20])[CH2:17][NH:18][CH2:7][C:6]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1

Participants

5

Reactant 3

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 2447283-Ethoxy-4-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 22226486HCID 22226486, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-ethoxy-4-methoxybenzaldehyde (3.6 g, 20 mmol) in ethanol (15 ml) is added to 2,2-dimethoxyethylamine (21 mmol) and the mixture heated at reflux for 2 hours. After cooling to room temperature, sodium borohydride (0.794 g, 21 mmol) is added and the mixture stirred at room temperature overnight. Ethanol is removed by evaporation and water added, followed by extraction with ethyl acetate. The organic extracts are combined, washed with water, brine, dried over magnesium sulfate and evaporated to give (2,2-dimethoxy-ethyl)-(3-ethoxy-4-methoxy-benzyl)-amine, [MH]+ 270. The intermediate (2.70 g, 10 mmol) is suspended in 6N HCl (50 ml), glyoxylic acid (0.88 g, 12 mmol) is added and the mixture heated for 1 hour at 100° C. After cooling to room temperature, methanol (30 ml) is added and the mixture filtered and characterised as the methyl ester M+ 276. The filtrate is treated with lithium hydroxide (10 mmol) in THF-methanol-water overnight. After evaporation of the solvents, the crude product is partitioned between water and dichloromethane. The aqueous phase is washed with dichloromethane and evaporated to dryness to afford (7-ethoxy-6-methoxy-isoquinolin-4-yl)-acetic acid lithium salt which is used for xanthine formation without further characterisation.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2 hours
  3. customEthanol is removed by evaporation and water
  4. additionadded
  5. extractionfollowed by extraction with ethyl acetate
  6. washwashed with water, brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-33555bfd542c4304b0086c81f0e935fb
Source dataset
uspto-grants-2008_04
Patent number
US07361661B2

Reaction notes

Loading…