Ammonium Chloride → (4-Amino-3-methoxy-benzyl)-benzyl-carbamic acid tert-butyl ester

HRID 1019753Notes

Reaction equation

[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([O:18][CH3:19])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>CO.[Zn]>[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([O:18][CH3:19])[CH:10]=1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of benzyl-(3-methoxy-4-nitro-benzyl)-carbamic acid tert-butyl ester (1.2 g, 3.22 mmol) in methanol (24 mL) was added a saturated aqueous solution of NH4Cl (24 mL) and zinc powder (1.05 g 16.11 mmol). The reaction was heated to 60° C. for 2 hours then the reaction mass was cooled to room temperature and filtered through celite. The solvents were removed under reduced pressure then the residue was partitioned between EtOAc (24 mL) and water (24 mL). The separated aqueous layer was extracted with EtOAc (12 ml), and then the combined organic extracts were washed with water (24 mL), brine (24 mL), dried (Na2SO4) and concentrated under reduced pressure to give the title compound (0.94 g, 85%).

Workup

temperaturethe reaction mass was cooled to room temperature
filtrationfiltered through celite
customThe solvents were removed under reduced pressure
customthe residue was partitioned between EtOAc (24 mL) and water (24 mL)
extractionThe separated aqueous layer was extracted with EtOAc (12 ml)
washthe combined organic extracts were washed with water (24 mL), brine (24 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9ffaba7b644846b1b1568756e4d7b2a6
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716287B2

Reaction notes

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