Water → HCID 86690534, compound

HRID 2172371Notes

Reaction equation

HRID 2172371 reaction equation
[CH2:1]([CH:3]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:4][N:5]1[C:17]2[CH:16]=[CH:15][C:14]3[CH:18]=[C:19]([C:22](=O)[C:23]4[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=4[CH3:31])[CH:20]=[CH:21][C:13]=3[C:12]=2[C:11]2[CH:10]=[C:9]([C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[CH3:41])=O)[CH:8]=[CH:7][C:6]1=2)[CH3:2].[Cl-].[OH:47][NH3+:48].[OH2:49]>N1C=CC=CC=1>[CH2:1]([CH:3]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:4][N:5]1[C:17]2[CH:16]=[CH:15][C:14]3[CH:18]=[C:19]([C:22](=[O:49])[C:23]4[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=4[CH3:31])[CH:20]=[CH:21][C:13]=3[C:12]=2[C:11]2[CH:10]=[C:9]([C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[CH3:41])=[N:48][OH:47])[CH:8]=[CH:7][C:6]1=2)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 21645Hydroxylamine HClHCID 66980798HCID 66980798, compound

Product 1

HCID 86690534HCID 86690534, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

To [7-(2-ethyl-hexyl)-3-(2,4,6-trimethylbenzoyl)-7H-benzo[c]carbazole-10-yl]-o-tolyl-methanone (0.25 g, 0.42 mmol) in pyridine (2 ml) is added hydroxylammonium chloride (59 mg, 0.84 mmol). The mixture is heated at 130° C., and then it is stirred for 6 hours. After the reaction mixture is cooled to room temperature, it is poured into water, and then the crude product is extracted with CH2Cl2 and washed with water and brine. After drying over MgSO4 and concentration, the desired product is obtained as a pale yellow solid (0.23 g, 90%). It is composed of an isomeric mixture, and the structure is confirmed by 1H-NMR spectrum (CDCl3) δ [ppm]: 0.84 (t), 0.92 (t), 1.23-1.40 (m), 2.05-2.07 (m), 2.10 (s), 2.18 (s), 2.20 (s), 2.40 (s), 4.32 (dd), 6.97 (s), 7.19 (dd), 7.34-7.38 (m), 7.42 (dd), 7.51 (dd), 7.62 (dd), 7.84 (d), 7.97 (d), 8.12 (dd), 8.61 (br), 9.06 (br).

Workup

  1. temperatureAfter the reaction mixture is cooled to room temperature
  2. extractionthe crude product is extracted with CH2Cl2
  3. washwashed with water and brine
  4. dry with materialAfter drying over MgSO4 and concentration

Sources & evidence

ORD record
ord-0929a1dfbad441f6b66756112c79c129
Source dataset
uspto-grants-2015_06
Patent number
US09051397B2

Reaction notes

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