Hydroxylamine HCl → HCID 86690535, compound

HRID 2172372Notes

Reaction equation

HRID 2172372 reaction equation
[CH2:1]([CH:3]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([N+:22]([O-:24])=[O:23])=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33])=O)[CH:10]=2)[CH3:2].[Cl-].[OH:39][NH3+:40]>N1C=CC=CC=1>[CH2:1]([CH:3]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([N+:22]([O-:24])=[O:23])=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33])=[N:40][OH:39])[CH:10]=2)[CH3:2]

Participants

4

Reactant 2

HCID 21645Hydroxylamine HClHCID 67130098HCID 67130098, compound

Product 1

HCID 86690535HCID 86690535, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To [11-(2-ethyl-hexyl)-5-nitro-11H-benzo[a]carbazole-8-yl]-o-tolyl-methanone (0.36 g, 0.73 mmol) in pyridine (6 ml) is added hydroxylammonium chloride (0.10 g, 1.45 mmol) at 120° C. After stirring for 16 hours, the reaction mixture is poured into ice-water. The crude is extracted with AcOEt, and washed with water and brine. After drying over MgSO4 and concentration, the crude is purified by column chromatography on silica gel eluting with CH2Cl2 to obtain a yellow resin (0.28 g, 76%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.79-0.90 (m), 1.13-1.48 (m), 2.21 (m), 2.29 (s), 4.69 (m), 7.25 (d), 7.37-7.47 (m), 7.55 (d), 7.67-7.75 (m), 7.90 (d), 8.04 (s), 8.60 (d), 8.89 (d), 8.92 (s).

Workup

  1. extractionThe crude is extracted with AcOEt
  2. washwashed with water and brine
  3. dry with materialAfter drying over MgSO4 and concentration
  4. customthe crude is purified by column chromatography on silica gel eluting with CH2Cl2

Sources & evidence

ORD record
ord-2a58e31bd88d481887cd50b84d0a654d
Source dataset
uspto-grants-2015_06
Patent number
US09051397B2

Reaction notes

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