Ammonium Chloride → Tert-butyl 2-(4-aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

HRID 2036718Notes

Reaction equation

HRID 2036718 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:21]=[CH:20][C:19]3[N:18]([CH3:22])[C:17]4[CH2:23][CH:24]5[NH:28][CH:27]([C:16]=4[C:15]=3[C:14]=2[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:26][CH2:25]5)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([S:10]([C:13]2[CH:21]=[CH:20][C:19]3[N:18]([CH3:22])[C:17]4[CH2:23][CH:24]5[NH:28][CH:27]([C:16]=4[C:15]=3[C:14]=2[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:26][CH2:25]5)(=[O:11])=[O:12])=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 67085545Tert-butyl 2-(4-nitrophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 67085509Tert-butyl 2-(4-aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylateYield 96%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of the product of step A (145 mg, 0.29 mmol), iron powder (82 mg, 1.45 mmol) and ammonium chloride (17 mg, 0.32 mmol) was taken up in ethanol (2.3 mL) and water (1.1 mL). The mixture was refluxed for 3 h then diluted with water and extracted with dichloromethane. The organic extract was dried over sodium sulfate and concentrated in vacuo to give tert-butyl 2-(4-aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (130 mg, 96%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.15 (s, 1H), 7.69-7.71 (m, 2H), 7.62 (d, J=9.3 Hz, 1H), 7.27 (d, J=8.7 Hz, 1H), 6.60-6.65 (m, 2H), 5.24 (br s, 1H), 4.69 (br s, 1H), 4.04 (br s, 2H), 3.58 (s, 3H), 3.48 (br s, 1H), 2.48 (d, J=16.5 Hz, 1H), 2.12-2.32 (m, 2H), 1.89-1.97 (m, 1H), 1.52-1.64 (m, 1H), 1.37 (br s, 9H).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. dry with materialwas dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-753711dfda614c61a38769c171bc8d16
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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