Water → 1-(6-Nitro-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-ethanone

HRID 1687041Notes

Reaction equation

HRID 1687041 reaction equation
[N+:1]([C:4]1[C:14]2[CH2:13][NH:12][CH2:11][CH2:10][NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:15](OC(=O)C)(=[O:17])[CH3:16].O>ClCCl>[N+:1]([C:4]1[C:14]2[CH2:13][N:12]([C:15](=[O:17])[CH3:16])[CH2:11][CH2:10][NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 578538166-Nitro-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine

Product 1

HCID 578538801-(6-Nitro-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-ethanoneYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Nitro-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine (140 mg, 0.74 mmol) was dissolved in dichloromethane (5 mL) and the mixture was treated with acetic anhydride (0.16 mL, 1.68 mmol). The reaction was then allowed to stir overnight at room temperature. The reaction mixture was then poured over water (10 mL) and organics were extracted with dichloromethane (3×10 mL). Combined organics were dried over Na2SO4, filtered and reduced. The crude product was then isolated and purified by flash column chromatography (0% MeOH/DCM-10% MeOH/DCM) to afford 120 mg of 1-(6-Nitro-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-ethanone as a yellow oil. LC/MS (ESI)=236.30 (M+H). 1H NMR (400 MHz, CDCl3) δ 7.26 (m, 2H), 7.07 (d, 1H, J=8.08 Hz), 6.86 (d, 1H, J=8.34 Hz), 5.95 (s, 1H), 4.64 (s, 2H), 3.55 (q, 2H, J=5.56 Hz), 3.33 (t, 2H, J=5.56 Hz), 1.97 (s, 3H).

Workup

  1. extractionorganics were extracted with dichloromethane (3×10 mL)
  2. dry with materialCombined organics were dried over Na2SO4
  3. filtrationfiltered
  4. customThe crude product was then isolated
  5. custompurified by flash column chromatography (0% MeOH/DCM-10% MeOH/DCM)

Sources & evidence

ORD record
ord-4f67fa9987704e7aaec0dafd0e28caa4
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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