Water → HCID 22622960, compound

HRID 840376Notes

Reaction equation

HRID 840376 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([CH2:13][CH2:14][NH2:15])[CH:11]=[CH:12][C:4]=2[O:3]1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O.[BH4-].[Na+].O>CO.O1CCCC1>[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([CH2:13][CH2:14][NH:15][CH2:20][C:19]3[CH:22]=[CH:23][CH:24]=[C:17]([Cl:16])[CH:18]=3)[CH:11]=[CH:12][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 114773-ChlorobenzaldehydeHCID 4311764Sodium borohydrideHCID 226231216-(2-Aminoethyl)-2-methyl-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 22622960HCID 22622960, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

915 mg (4.437 mmol) of 2-methyl-3-oxo-6-(2-amino-ethyl)-3,4-dihydro-2H-1,4-benzoxazine is dissolved in 16 ml of a methanol/tetrahydrofuran mixture (4:1). After adding 623.7 mg (4.437 mmol) of 3-chlorobenzaldehyde, the batch is stirred for two hours at room temperature. Then, 91.1 mg (2.408 mmol) of sodium borohydride is added in portions and stirred for another two hours at room temperature. The batch is added to 50 ml of water, and after three-fold extraction with ethyl acetate, the combined organic extracts are washed with brine, dried and the solvent is spun off. The remaining residue is chromatographed on silica gel (mobile solvent: ethyl acetate/methanol). Yield 584.6 mg (39.8%).

Workup

  1. stirringstirred for another two hours at room temperature
  2. extractionafter three-fold extraction with ethyl acetate
  3. washthe combined organic extracts are washed with brine
  4. customdried
  5. customThe remaining residue is chromatographed on silica gel (mobile solvent: ethyl acetate/methanol)

Sources & evidence

ORD record
ord-c8e2d6dfa3e54925b61e5bcd7a265cb0
Source dataset
uspto-grants-2002_04
Patent number
US06365736B1

Reaction notes

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