Methanol → HCID 67263839, compound

HRID 1687815Notes

Reaction equation

HRID 1687815 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[N:13]([CH2:23][CH3:24])[CH2:14][CH2:15][NH:16][C:17](=[O:22])C(F)(F)F.CO.C[O-].[Na+]>>[CH2:23]([N:13]1[C:5]2[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:4]=2[C:17](=[O:22])[NH:16][CH2:15][CH2:14]1)[CH3:24]

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium Methoxide2×HCID 86634044HCID 86634044, compound

Product 1

HCID 67263839HCID 67263839, compoundYield 72.1%

Procedure

Into a round bottom flask, 2-{ethyl-[2-(2,2,2-trifluoro-acetylamino)-ethyl]-amino}-4-nitro-benzoic acid methyl ester (4.80 g, 13.2 mmol), methanol (60.0 mL, 1480 mmol) and sodium methoxide (0.86 g, 16 mmol) were added. The reaction was heated to 50 degree for 18 hours. TLC suggested 50% conversion. sodium methoxide (0.86 g, 16 mmoles) was added. The reaction was heated to reflux for 4 hours. The reaction was partitioned with water and DCM. The organic was separated, washed with Brine, and dried over magnesium sulfate. The solid was filtered and washed with DCM. The organic was removed under vacuum to afford 1-ethyl-8-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one as a yellow solid (2.24 g, 71%). 1H-NMR (DMSO-D6, 400 MHz): δ 8.48 (t, 1H), 7.72 (d, 1H), 7.65 (d, 1H), 7.64 (s, 1H), 3.18-3.32 (m, 6H), 1.15 (t, 3H)

Workup

  1. temperatureThe reaction was heated to 50 degree for 18 hours
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 4 hours
  4. customThe reaction was partitioned with water and DCM
  5. customThe organic was separated
  6. washwashed with Brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe solid was filtered
  9. washwashed with DCM
  10. customThe organic was removed under vacuum

Sources & evidence

ORD record
ord-ecc9969dc974475f98c785527e12bbee
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…