Calcium Chloride → tert-butyl 9-amino-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

HRID 1591942Notes

Reaction equation

HRID 1591942 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C:8]3[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17][C:7]=3[C:6]=2[CH:5]=1)([O-])=O.[Cl-].[Ca+2].[Cl-]>C(O)C.[Zn]>[NH2:1][C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C:8]3[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17][C:7]=3[C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 5284359Calcium ChlorideHCID 58997625tert-butyl 9-nitro-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

Product 1

HCID 58997626tert-butyl 9-amino-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 9-nitro-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.25 g, 0.75 mmol), zinc (1.48 g, 22.6 mmol) and calcium chloride (0.04 g, 0.38 mmol) in 78% ethanol (7.5 mL) was refluxed for 2 h and filtered hot. The filtrate was concentrated in vacuo to dryness to give 0.22 g (99%) of solid as the desired product: MS (EI) m/z 302 (MH+).

Workup

  1. temperaturewas refluxed for 2 h
  2. filtrationfiltered hot
  3. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-fdf6137bd0ce4160b500ddaab9864ef3
Source dataset
uspto-grants-2007_11
Patent number
US07291738B2

Reaction notes

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