Ethyl Acetate → Tert-butyl 2-(3-(aminomethyl)-4-(4-(3,4-dichlorobenzamido)phenoxy)phenyl)acetate

HRID 1927718Notes

Reaction equation

HRID 1927718 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)=[CH:12][CH:11]=1)#[N:2].C(OCC)(=O)C>N.CO.[Ni]>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 68467168HCID 68467168, compound

Product 1

HCID 68470120Tert-butyl 2-(3-(aminomethyl)-4-(4-(3,4-dichlorobenzamido)phenoxy)phenyl)acetateYield 99.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

The product of step B (100 mg, 0.201 mmol) was diluted with 7N ammonia/methanol (10 mL), followed by addition of ethyl acetate (10 mL). Once the material dissolved, Raney Nickel (1.72 mg, 0.0201 mmol) was added and the reaction was purged three times with a balloon of hydrogen. After stirring for 12 hours, the reaction mixture was filtered through a GF/F filter and concentrated. The residue was purified using a biotage 12i column eluting with methylene chloride:MeOH:NH4OH (90:9:1) to yield tert-butyl 2-(3-(aminomethyl)-4-(4-(3,4-dichlorobenzamido)phenoxy)phenyl)acetate (100 mg, 99.2% yield) as a clear oil.

Workup

  1. dissolutionOnce the material dissolved
  2. customthe reaction was purged three times with a balloon of hydrogen
  3. filtrationthe reaction mixture was filtered through a GF/F
  4. filtrationfilter
  5. concentrationconcentrated
  6. customThe residue was purified
  7. washeluting with methylene chloride:MeOH:NH4OH (90:9:1)

Sources & evidence

ORD record
ord-191597e58c9c4fd5819150c588db8b88
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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