1,3-Dihydro-5-(2-chlorophenyl)-2H-1,4-benzodiozepin-2-one → 1,3-dihydro-5-(o-bromophenyl)-2H-1,4-benzodiazepin-2-one

HRID 328717Notes

Reaction equation

HRID 328717 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[O:19])[CH2:10][N:9]=1.[Br:20]C1C=CC=CC=1C(C1C=CC=CC=1[N+]([O-])=O)=O.NC1C=CC=CC=1C(C1C=CC=CC=1Br)=O>>[Br:20][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[O:19])[CH2:10][N:9]=1

Participants

4

Reactant 3

HCID 145904461,3-Dihydro-5-(2-chlorophenyl)-2H-1,4-benzodiozepin-2-oneHCID 20200331(2-Aminophenyl)(2-bromophenyl)methanoneHCID 218770322-Bromo-2'-nitrobenzophenone

Product 1

HCID 214401071,3-dihydro-5-(o-bromophenyl)-2H-1,4-benzodiazepin-2-one

Procedure

To make the 6-(o-bromophenyl) product one can follow the procedure shown by Sternbach et al., J. Med. Chem. 6, 263 (1963), for the preparation of 1,3-dihydro-5-(o-chlorophenyl)-2H-1,4-benzodiazepin-2-one using the Sandmeyer reaction followed by catalytic hydrogenation of the resulting 2-bromo-2'-nitrobenzophenone. This product, 2-amino-2'-bromobenzophenone, can be substituted in the process described by Sternbach et al. to produce 1,3-dihydro-5-(o-bromophenyl)-2H-1,4-benzodiazepin-2-one.

Workup

  1. customthe Sandmeyer reaction

Sources & evidence

ORD record
ord-f6c6e6ca99894b43aa2a59f97658fa32
Source dataset
uspto-grants-1977_04
Patent number
US04018788

Reaction notes

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