Water → 3-Chloro-4-(2-hydroxy-1-methyl-ethylamino)-benzonitrile

HRID 2094317Notes

Reaction equation

HRID 2094317 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[NH2:11][CH:12]([CH3:15])[CH2:13][OH:14].O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:11][CH:12]([CH3:15])[CH2:13][OH:14])[C:5]#[N:6]

Participants

5

Reactant 3

HCID 962WaterHCID 51262-AminopropanolHCID 1455253-Chloro-4-fluorobenzonitrile

Product 1

HCID 630942843-Chloro-4-(2-hydroxy-1-methyl-ethylamino)-benzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.00 g (25.7 mmol) 3-chloro-4-fluoro-benzonitrile are heated to 60° C. in 20 ml DMSO with 8.00 g (106.5 mmol) 2-amino-1-propanol with stirring for 2 hours. Then the reaction mixture is poured into water and extracted with ethyl acetate. The combined organic phases are washed with water and sat. sodium chloride solution, dried over sodium sulphate and evaporated down i. vac.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases are washed with water and sat. sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customevaporated down i

Sources & evidence

ORD record
ord-68bc354c1ee14f33bb585288027ecd35
Source dataset
uspto-grants-2013_05
Patent number
US08445525B2

Reaction notes

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