(2-Methoxyethyl)(methyl)amine → HCID 19592956, compound

HRID 613498Notes

Reaction equation

HRID 613498 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2C=O)=[O:5].[CH3:24][O:25][CH2:26][CH2:27][NH:28][CH3:29].[C:30](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[Cl:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:2]([Cl:1])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[CH2:29][N:28]([CH2:27][CH2:26][O:25][CH3:24])[CH3:30])=[O:5]

Participants

5

Reactant 3

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 5049666Sodium triacetoxyborohydrideHCID 19592298HCID 19592298, compound

Product 1

HCID 19592956HCID 19592956, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred suspension of 8-(2,6-dichlorobenzoylamino)-4-formylquinoline (100 mg), N-(2-methoxyethyl)methylamine (28 mg) and acetic acid (17 mg) was added sodium triacetoxyborohydride (91.6 mg) portionwise over a period of 5 minutes at ambient temperature, and the resulting mixture was stirred at the same temperature for four hours. The crude product was partitioned in dichloromethane and aqueous saturated sodium bicarbonate solution. The organic phase was dried over anhydrous magnesium sulfate, filtered, evaporated under reduced pressure. The residue was purified by a preparative thin layer chromatography (5%0 methanoldichloromethane) and recrystallized from ethanol to give 8-(2,6-dichlorobenzoylamino)-4-[N-(2-methoxyethyl)-N-methylaminomethyl]quinoline (77 mg) as a colorless powder.

Workup

  1. customThe crude product was partitioned in dichloromethane
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by a preparative thin layer chromatography (5%0 methanoldichloromethane)
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6bac48483c99409e8dfe5298e10f36f4
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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