Sodium Methoxide → 4-METHYL-1,3,4,5-TETRAHYDRO-2H-1,5-BENZODIAZEPIN-2-ONE

HRID 1485475Notes

Reaction equation

HRID 1485475 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH:9]([CH3:16])[CH2:10][C:11](OCC)=[O:12].C[O-].[Na+]>CO>[CH3:16][CH:9]1[CH2:10][C:11](=[O:12])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86718509HCID 86718509, compound

Product 1

HCID 198684-METHYL-1,3,4,5-TETRAHYDRO-2H-1,5-BENZODIAZEPIN-2-ONEYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An round bottomed flask was charged with ethyl 3-(2-aminophenylamino)butanoate (684 mg, 3.08 mmol) and a stirbar. MeOH (15 mL, 0.1 M) was added, followed by sodium methoxide (249 mg, 4.62 mmol), and the solution was stirred at reflux for 48 h. The mixture was concentrated with celite and purified by silica gel chromatography (eluting with hexanes/ethyl acetate) to yield 4-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one as an off-white amorphous solid (0.22 g, 1.25 mmol, 41%).

Workup

  1. temperatureat reflux for 48 h
  2. concentrationThe mixture was concentrated with celite
  3. custompurified by silica gel chromatography (eluting with hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-d71043cd0fc648ea9d2966ce04accddb
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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