Methanol → 2,4-Dichloro-6-methoxymethylbenzylamine
Reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH2:11][O:12][CH3:13])[C:3]=1[C:4]#[N:5].CO.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH2:11][O:12][CH3:13])[C:3]=1[CH2:4][NH2:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A solution of BH3 (3.5 mL, 1M in THF) was added to a solution of 2,4-dichloro-6-(methoxymethyl)benzonitrile (0.88 mmol) in 3 mL THF. The reaction mixture was heated to 60° C. for 2 h. At 0° C., 3.5 mL MeOH was dropwise added and the mixture was stirred until gas evolution was finished. An aq. solution of 10% NaOH was added still under cooling. The solvent was removed under vacuo, the residue was diluted with water and extracted 3 times with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as orange oil.
Workup
- temperatureunder cooling
- customThe solvent was removed under vacuo
- additionthe residue was diluted with water
- extractionextracted 3 times with EtOAc
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-427439c804e14e3f9aeb2294674b3934
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409917B2
Reaction notes
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