Water → (1R,2R)-1-Amino-6-nitro-2,3-dihydro-1H-inden-2-ol

HRID 324986Notes

Reaction equation

HRID 324986 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH:9]3[O:13][CH:10]32)=[CH:6][CH:5]=1)([O-:3])=[O:2].O.[Cl-].[Na+].[OH-].[NH4+:18]>>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][C@@H:9]([OH:13])[C@@H:10]2[NH2:18])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 14923Ammonium HydroxideHCID 148964001,2-Epoxy-6-nitroindane

Product 1

HCID 11356015(1R,2R)-1-Amino-6-nitro-2,3-dihydro-1H-inden-2-ol

Conditions

Temperature
45 °C

Procedure

A suspension of 6-nitro-1,2-epoxyindane in concentrated ammonium hydroxide (250 mL) was heated overnight in an oil bath at 45° C. The next day water was added and the basic aqueous layer was saturated with sodium chloride. The cloudy reaction mixture was extracted with tetrahydrofuran until no more product could be seen in the aqueous layer by TLC. The organic layers were combined, dried over magnesium sulfate, filtered, concentrated, and recrystallized from ethyl acetate to give 11.54 g of the title compound. (91% over two steps).

Workup

  1. customThe cloudy reaction mixture
  2. extractionwas extracted with tetrahydrofuran until no more product
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3c7b15b8d2b1496ca5d74e4b1a229f62
Source dataset
uspto-grants-2001_04
Patent number
US06221876B1

Reaction notes

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