Sodium Hydroxide → (3-Amino-4-chlorophenyl)methanol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[N+:10]([O-])=O.[OH-].[Na+]>CO.Cl.[Fe]>[NH2:10][C:3]1[CH:4]=[C:5]([CH2:8][OH:9])[CH:6]=[CH:7][C:2]=1[Cl:1]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 65 °C
Procedure
To a solution of (4-chloro-3-nitro-phenyl)-methanol (4.96 g, 26.4 mmol) in MeOH (60 mL) and conc HCl (22 ml) was added iron powder (4.43 g, 3 eq) in portions. The mixture was then heated at reflux (65° C.) for 6 h, cooled and poured on ice water. The solution was neutralised with dilute NaOH and filtered. The filtrate was extracted with EA several times. The combined organic layers were washed with brine, dried over MgSO4 and concentrated. The product was recovered as a greyish solid (3.8 g, 92%).
Workup
- temperatureThe mixture was then heated
- temperaturecooled
- additionpoured on ice water
- filtrationfiltered
- extractionThe filtrate was extracted with EA several times
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe product was recovered as a greyish solid (3.8 g, 92%)
Sources & evidence
- ORD record
- ord-9855c843ba7743eba945fe703fb536b8
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003654B2
Reaction notes
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