Ammonium Chloride → HCID 66834635, compound

HRID 61818Notes

Reaction equation

HRID 61818 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]3[C:30](=[O:31])[C:29]4[C:28]5[C:23](=[CH:24][CH:25]=[C:26]([N+:32]([O-])=O)[CH:27]=5)[NH:22][C:21]=4[C:20]([CH3:36])([CH3:35])[C:19]=3[CH:37]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>[Fe].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]3[C:30](=[O:31])[C:29]4[C:28]5[C:23](=[CH:24][CH:25]=[C:26]([NH2:32])[CH:27]=5)[NH:22][C:21]=4[C:20]([CH3:36])([CH3:35])[C:19]=3[CH:37]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 66834037HCID 66834037, compound

Product 1

HCID 66834635HCID 66834635, compoundYield 118.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To the ethanol (8 ml) suspension of 4-(6,6-dimethyl-2-nitro-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-8-yl oxy)-piperidine-1-carboxylic acid tert-butyl ester (Compound P4, 103 mg, 0.204 mmol), iron powder (228 mg, 20 eq.), ammonium chloride (109 mg, 10 eq.), and distilled water (4 ml) were added and the mixture was stirred at 90° C. for 30 min. Upon the completion of the reaction, insoluble matters were filtered off, and the filtrate was extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (115 mg, 57%).

Workup

  1. distillationdistilled water (4 ml)
  2. additionwere added
  3. customUpon the completion of the reaction, insoluble matters
  4. filtrationwere filtered off
  5. extractionthe filtrate was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customThe drying agent was removed by filtration
  9. customthe residues obtained
  10. concentrationafter concentration under reduced pressure
  11. customwere purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6061df8aa23848348153dec3897e4901
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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