Sulfuric acid magnesium salt (1:1) → Methyl 2-((7-methoxyquinolin-4-ylmethyl)amino)propanoate

HRID 899969Notes

Reaction equation

HRID 899969 reaction equation
Cl.[NH2:2][C:3]([CH3:9])(C)[C:4]([O:6][CH3:7])=[O:5].S([O-])([O-])(=O)=O.[Mg+2].[CH3:16][O:17][C:18]1[CH:27]=[C:26]2[C:21]([C:22]([CH:28]=O)=[CH:23][CH:24]=[N:25]2)=[CH:20][CH:19]=1.[BH4-].[Na+]>ClCCl.CCOC(C)=O.C(N(CC)CC)C>[CH3:16][O:17][C:18]1[CH:27]=[C:26]2[C:21]([C:22]([CH2:28][NH:2][CH:3]([CH3:9])[C:4]([O:6][CH3:7])=[O:5])=[CH:23][CH:24]=[N:25]2)=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 13258034Methyl 2-aminoisobutyrate hydrochlorideHCID 177506557-Methoxyquinoline-4-carbaldehyde

Product 1

HCID 68763550Methyl 2-((7-methoxyquinolin-4-ylmethyl)amino)propanoateYield 43.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1.23 g of methyl α-aminoisobutyrate hydrochloride and 1.12 ml of triethylamine in 30 ml of dichloromethane is stirred at 0° C. for 20 minutes. Next, 1 g of magnesium sulfate and 1.5 g of 7-methoxyquinoline-4-carbaldehyde are added. Stirring is continued for 15 hours at room temperature and the mixture is then concentrated under reduced pressure. The residue is taken up in 35 ml of methanol, the solution obtained is cooled to 0° C. and 0.31 g of sodium borohydride is then added portionwise. The reaction medium is stirred at a temperature in the region of 20° C. for 15 hours. The reaction medium is concentrated under reduced pressure. The residue obtained is taken up in 100 ml of EtOAc. The precipitate formed is filtered off and the filtrate is concentrated under reduced pressure and then purified by flash chromatography on a column (SiO2, EtOAc as eluent, Ar), and 0.95 g of the expected product is obtained.

Workup

  1. stirringStirring
  2. waitis continued for 15 hours at room temperature
  3. concentrationthe mixture is then concentrated under reduced pressure
  4. customthe solution obtained
  5. temperatureis cooled to 0° C.
  6. stirringThe reaction medium is stirred at a temperature in the region of 20° C. for 15 hours
  7. concentrationThe reaction medium is concentrated under reduced pressure
  8. customThe residue obtained
  9. customThe precipitate formed
  10. filtrationis filtered off
  11. concentrationthe filtrate is concentrated under reduced pressure
  12. custompurified by flash chromatography on a column (SiO2, EtOAc as eluent, Ar)

Sources & evidence

ORD record
ord-df47dd0e9f4446018c464f99cb3b85b4
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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