Ammonium Chloride → Benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)ethyl)-2-methylphenylcarbamate

HRID 2361272Notes

Reaction equation

HRID 2361272 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH:15]([C:20]3[C:21]([CH3:37])=[C:22]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:23]=[CH:24][CH:25]=3)[CH2:16][N+:17]([O-])=O)=[CH:11][NH:12]2)=[CH:8][CH:7]=1.[Cl-].[NH4+]>O1CCCC1.CO.C(OCC)(=O)C.[Zn]>[NH2:17][CH2:16][CH:15]([C:20]1[C:21]([CH3:37])=[C:22]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:23]=[CH:24][CH:25]=1)[C:10]1[C:9]2[C:13](=[CH:14][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][CH:8]=2)[NH:12][CH:11]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 67994685Benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitroethyl)-2-methylphenylcarbamate

Product 1

HCID 67994818Benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)ethyl)-2-methylphenylcarbamateYield 100%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitroethyl)-2-methylphenylcarbamate (1.75 g, 3.48 mmol), ammonium chloride (2.79 g, 52.1 mmol), and zinc dust (3.41 g, 52.1 mmol) in tetrahydrofuran (35 mL) and methanol (35 mL) was stirred at room temperature for 4.5 hr. The mixture was diluted with ethyl acetate (40 mL) and filtered through CELITE®. The filtrate was concentrated under vacuum, and the residue was diluted with water (40 mL), basified with saturated NaHCO3 solution, and extracted with ethyl acetate (4×40 mL). The combined extract was washed with brine (40 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (1.65 g, 3.48 mmol, 100% yield) as beige solid.

Workup

  1. filtrationfiltered through CELITE®
  2. concentrationThe filtrate was concentrated under vacuum
  3. additionthe residue was diluted with water (40 mL)
  4. extractionextracted with ethyl acetate (4×40 mL)
  5. extractionThe combined extract
  6. washwas washed with brine (40 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-3515c6bef63c4f1fa893ea62ecdfe660
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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