Potassium Bromide → 7,12-Dihydropyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one

HRID 2425864Notes

Reaction equation

HRID 2425864 reaction equation
C1(N[N:8]=[C:9]2[CH2:15][CH2:14][C:13](=[O:16])[NH:12][C:11]3[CH:17]=[CH:18][CH:19]=[N:20][C:10]2=3)C=CC=CC=1.[K+].[Br-].[C:23](#N)[CH3:24].O>C1(OC2C=CC=CC=2)C=CC=CC=1>[N:20]1[C:10]2[C:9]3[NH:8][C:24]4[C:23]([C:15]=3[CH2:14][C:13](=[O:16])[NH:12][C:11]=2[CH:17]=[CH:18][CH:19]=1)=[CH:11][CH:10]=[CH:9][CH:15]=4

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 18373917Acetonitrile--water (1/1)HCID 1363439317,8-Dihydro-5H-pyrido[3,2-b]azepine-6,9-dione 9-(phenylhydrazone)

Product 1

HCID 248281727,12-Dihydropyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Prepared according to general procedure B from 72.4 mg (0.27 mmol) 7,8-dihydro-5H-pyrido[3,2-b]azepine-6,9-dione 9-(phenylhydrazone) in 30 ml diphenyl ether. Recrystallization from ethanol afforded a brown solid. Yield: 17 mg (25%); m.p. >330° C.; IR (KBr): 3054 cm−1 (CH-arom.), 2974 cm−1 (CH-aliph.), 1675 cm−1 (C═O), 1H-NMR (d6-DMSO, 400 MHz): δ (ppm)=3.66 (s, 2H, azepine-CH2), 7.06-7.09 (m, 1H, arom. H), 7.18-7.22 (m, 1H, arom. H), 7.40 (dd, 1H, 8.2/4.5 Hz, arom. H), 7.47 (d, 1H, 8.2 Hz, arom. H), 7.62 (dd, 1H, 8.2/1.4 Hz, arom. H), 7.70 (d, 1H, 8.0 Hz, arom. H), 8.48 (dd, 1H, 4.5/1.4 Hz, arom. H), 10.22 (s, 1H, NH), 11.70 (s, 1H, NH); 13C-NMR (DMSO-d6, 100.6 MHz): δ (ppm)=31.9 (azepine-CH2), 111.9, 118.4, 119.1, 122.5, 122.8, 129.3, 144.3 (tert. arom. C), 108.9, 126.3, 132.0, 132.5, 137.5, 140.5 (quat. arom. C), 171.1 (C═O); C15H11N3O (249.27); purity (HPLC): 98.8% (ts=3.25 min, acetonitrile/water 35:65).

Workup

  1. customPrepared
  2. customRecrystallization from ethanol
  3. customafforded a brown solid

Sources & evidence

ORD record
ord-c765470b21964013a886c7b402f42a02
Source dataset
uspto-grants-2011_06
Patent number
US07968535B2

Reaction notes

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