Nitric Acid → HCID 14817945, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[N+:11]([O-:14])(O)=[O:12].[CH3:15][C:16](OC(C)=O)=[O:17]>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:16](=[O:17])[CH3:15])=[CH:4][C:3]=1[N+:11]([O-:14])=[O:12]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
2-(4-Aminophenyl)ethanol (186) (Aldrich, 26,164-5) (2.4 g, 17.5 mmol) was dissolved in Ac2O (12 mL) and chilled to 0° C. before addition of concentrated HNO3 (2.5 mL). The colorless solution turned red as it was stirred at 0° C. After stirring for 10 min, the reaction was quenched by addition of ice cold water (50 mL). The resulting biphasic mixture was stirred for 0.5 h to provide for 187 as a solid. The solid was recovered by filtration and recrystallized from methanol to give 187 (2.13 g) as a crystalline solid.
Workup
- stirringAfter stirring for 10 min
- customthe reaction was quenched by addition of ice cold water (50 mL)
- stirringThe resulting biphasic mixture was stirred for 0.5 h
Sources & evidence
- ORD record
- ord-4e3b03bf3dd642818734dd5f3e6dc302
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07417152B2
Reaction notes
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