Potassium Bromide → 7,8-Dihydro-5H-pyrido[3,2-b]azepine-6,9-dione 9-[(3,5-dichlorophenyl)hydrazone]

HRID 2425861Notes

Reaction equation

HRID 2425861 reaction equation
[N:1]1[C:11]2[C:10](=O)[CH2:9][CH2:8][C:7](=[O:13])[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[Cl:15][C:16]1[CH:17]=[C:18]([NH:23][NH2:24])[CH:19]=[C:20]([Cl:22])[CH:21]=1.C([O-])(=O)C.[Na+].[K+].[Br-]>>[Cl:15][C:16]1[CH:17]=[C:18]([NH:23][N:24]=[C:10]2[CH2:9][CH2:8][C:7](=[O:13])[NH:6][C:5]3[CH:4]=[CH:3][CH:2]=[N:1][C:11]2=3)[CH:19]=[C:20]([Cl:22])[CH:21]=1

Participants

5

Reactant 4

HCID 253877Potassium BromideHCID 517045Sodium AcetateHCID 2723913(3,5-Dichlorophenyl)hydrazine monohydrochlorideHCID 457893917,8-Dihydro-5H-pyrido[3,2-B]azepine-6,9-dione

Product 1

HCID 1363439297,8-Dihydro-5H-pyrido[3,2-b]azepine-6,9-dione 9-[(3,5-dichlorophenyl)hydrazone]

Procedure

Prepared according to general procedure A from 338.5 mg (1.92 mmol) 5H-pyrido[3,2-b]azepine-6,9(7H,8H)-dione, 452 mg (2.11 mmol) (3,5-dichlorophenyl)hydrazine hydrochloride, and 169 mg (2.11 mmol) sodium acetate. Recrystallization from ethanol afforded a beige powder. Yield: 213 mg (33%); m.p. 270° C. (dec.); IR (KBr): 3281 cm−1 (NH), 3067/3029 cm−1 (CH-arom.), 2892 cm−1 (CH-aliph.), 1671 cm−1 (C═O); 1H-NMR (DMSO-d6, 400 MHz): δ (ppm)=2.57-2.60 (m, 2H, azepine-CH2, part of AA′XX′-system), 3.02-3.05 (m, 2H, azepine-CH2, part of AA′XX′-system), 6.91-6.92 (m, 1H, arom. H), 7.16 (d, 2H, 1.9 Hz, arom. H), 7.37-7.44 (m, 2H, arom. H), 8.44 (dd, 1H, 4.2/1.8 Hz, arom. H), 9.72 (s, 1H, NH), 9.81 (s, 1H, NH); C15H12Cl2N4O (335.20).

Workup

  1. customPrepared
  2. customRecrystallization from ethanol
  3. customafforded a beige powder

Sources & evidence

ORD record
ord-7a8a7b43bc234a209a7dbda614770635
Source dataset
uspto-grants-2011_06
Patent number
US07968535B2

Reaction notes

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