Nitronium tetrafluoroborate → 5-Acetyl-2-chloro-5,11-dihydro-11-ethyl-4-methyl-3-nitro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 53557Notes

Reaction equation

HRID 53557 reaction equation
[C:1]([N:4]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[N:15][C:8]=2[N:7]([CH2:16][CH3:17])[C:6]2[N:18]=[C:19]([Cl:23])[CH:20]=[C:21]([CH3:22])[C:5]1=2)(=[O:3])[CH3:2].F[B-](F)(F)F.[O:29]=[N+:30]=[O:31]>C(#N)C>[C:1]([N:4]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[N:15][C:8]=2[N:7]([CH2:16][CH3:17])[C:6]2[N:18]=[C:19]([Cl:23])[C:20]([N+:30]([O-:31])=[O:29])=[C:21]([CH3:22])[C:5]1=2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11073463Nitronium tetrafluoroborateHCID 199600515-acetyl-2-chloro-5,11-dihydro-11-ethyl-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Product 1

HCID 199600225-Acetyl-2-chloro-5,11-dihydro-11-ethyl-4-methyl-3-nitro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneYield 18.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-acetyl-2-chloro-5,11-dihydro-11-ethyl-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (3.36 g) in acetonitrile (20 mL) cooled on ice was added nitronium tetrafluoroborate (85%, 2.26 g). The mixture was removed from the ice bath and was stirred for 5 hours. The reaction then was quenched with 10% potassium carbonate. Ethyl acetate was added and the organic phase was separated, washed, dried, and evaporated. Chromatography over silica gel gave 0.71 g of the title compound, which crystallized from diisopropyl ether, m.p. 140-141.

Workup

  1. customThe mixture was removed from the ice bath
  2. customThe reaction
  3. customthen was quenched with 10% potassium carbonate
  4. additionEthyl acetate was added
  5. customthe organic phase was separated
  6. washwashed
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-12e9883a74144360b23be1e7a0dbdb0e
Source dataset
uspto-grants-1997_04
Patent number
US05620974

Reaction notes

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