Methyl 2-bromo-3-nitrobenzoate → 9-Nitro-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-one

HRID 326878Notes

Reaction equation

HRID 326878 reaction equation
Br[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.O.[CH2:16]([NH2:19])[CH2:17][NH2:18]>C(O)CCC>[N+:12]([C:11]1[C:2]2[NH:19][CH2:16][CH2:17][NH:18][C:4](=[O:6])[C:3]=2[CH:8]=[CH:9][CH:10]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 79263Methyl 2-bromo-3-nitrobenzoateHCID 12200817Ethylenediamine monohydrate

Product 1

HCID 27716119-Nitro-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-one

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 11.7 parts of methyl 2-bromo-3-nitrobenzoate, 8.1 parts of 1,2-ethanediamine monohydrate and 40 parts of 1-butanol was stirred for 1/2 hour at reflux temperature. The reaction mixture was evaporated and the residue was diluted with 50 parts of water. The precipitate was filtered off and washed with water and 2-propanol. It was then recrystallized from 2-methoxyethanol, yielding 6.5 parts of 2,3,4,5-tetrahydro-9-nitro-1H-1,4-benzodiazepin-5-one; mp. 191°-195° C. (interm. 1)

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. additionthe residue was diluted with 50 parts of water
  4. filtrationThe precipitate was filtered off
  5. washwashed with water and 2-propanol
  6. customIt was then recrystallized from 2-methoxyethanol

Sources & evidence

ORD record
ord-6d2eab94fff14ac4bd1de5080b243cca
Source dataset
uspto-grants-1993_12
Patent number
US05270464

Reaction notes

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