Water → 2-(2-Methoxyethoxy)-6-nitroaniline
Reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].Br[CH2:13][CH2:14][O:15][CH3:16].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:16][O:15][CH2:14][CH2:13][O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH2:1]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5 g 2-Amino-3-nitro-phenol, 4.5 g 1-Bromo-2-methoxy-ethane, 4.4 g K2CO3 in 50 mL DMF were heated to 60° C. for 16 h. Then 50 mL of water were added and the mixture was extracted with ethyl acetate (3×100 ml). The combined organic layers were dried over MgSO4, and the solvents were removed under reduced pressure. The remaining product was pure enough for the next reaction step. Yield: 5.8 g.
Workup
- extractionthe mixture was extracted with ethyl acetate (3×100 ml)
- dry with materialThe combined organic layers were dried over MgSO4
- customthe solvents were removed under reduced pressure
- customThe remaining product was pure enough for the next reaction step
Sources & evidence
- ORD record
- ord-e4212dad419940b0b09a993a75280f66
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741341B2
Reaction notes
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