Sodium → 2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

HRID 1485392Notes

Reaction equation

HRID 1485392 reaction equation
[Na].[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][CH2:10][CH2:11][C:12]([O:14]C)=O>CO>[NH:2]1[C:12](=[O:14])[CH2:11][CH2:10][NH:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]1=2

Participants

4

Reactant 2

HCID 5360545SodiumHCID 57323377HCID 57323377, compound

Product 1

HCID 2237712,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-oneYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium (1.8 g, 77.2 mmol) was added in portions to methanol (50 mL), and the mixture was stirred for 1 h. The resulting mixture was added dropwise to a solution of methyl 3-((2-aminophenyl)amino)propanoate (9.4 g, 48.2 mmol) in methanol (150 mL) at 0° C. Once addition was completed, the mixture was stirred at room temperature overnight. The mixture was concentrated, and the residue was purified by CombiFlash (PE:EA=5:1) to give 4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one as a yellow solid (3.9 g, 50%). LRMS (M+H)+: 161 m/z. 1H NMR (300 MHz, CD3OD): δ 2.61 (t, J=6.0 Hz, 2H), 3.62 (t, J=6.0 Hz, 2H), 6.76-6.86 (m, 2H), 6.90-6.99 (m, 2H).

Workup

  1. additionOnce addition
  2. stirringthe mixture was stirred at room temperature overnight
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by CombiFlash (PE:EA=5:1)

Sources & evidence

ORD record
ord-a306565024034b7f8c483d63889045d4
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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