Ammonium Chloride → HCID 90241078, compound

HRID 2202036Notes

Reaction equation

HRID 2202036 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH:12]([OH:27])[CH2:13][NH:14][C:15](=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[C:17]=1[CH3:25].[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:22][C:18]1[C:17]([CH3:25])=[C:16]([CH:21]=[CH:20][CH:19]=1)[C:15]([NH:14][CH2:13][CH:12]([OH:27])[CH2:11][N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)=[O:26]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 90241885HCID 90241885, compound

Product 1

HCID 90241078HCID 90241078, compoundYield 95.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)-2-methyl-3-nitrobenzamide (1.6 g, 4.3 mmol) in EtOH (15 mL) and H2O (15 mL) was added Fe powder (1.45 g, 25.8 mmol) and NH4Cl (1.38 g, 25.8 mmol). The mixture was stirred at 60° C. for 4 h. The reaction solution was filtered, and the filtrate was concentrated to remove EtOH. The residue was diluted with water and extracted with DCM. The organic layer was concentrated to give the desired product (1.4 g, Yield 95.9%). The crude product was used in next step without further purification. LCMS (m/z): 340.1 (M+H).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customto remove EtOH
  4. additionThe residue was diluted with water
  5. extractionextracted with DCM
  6. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-b4aa467ab863443d849df1cca3d5dbf8
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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