Sodium Hydroxide → HCID 21184825, compound

HRID 568051Notes

Reaction equation

HRID 568051 reaction equation
[OH:1][CH:2]1[CH:10]([N+:11]([O-])=O)[C:9]2[CH2:8][C:7](=[O:14])[CH:6]=[CH:5][C:4]=2[CH2:3]1.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[NH2:11][CH:10]1[C:9]2[CH2:8][C:7](=[O:14])[CH:6]=[CH:5][C:4]=2[CH2:3][CH:2]1[OH:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 21184591HCID 21184591, compound

Product 1

HCID 21184825HCID 21184825, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-hydroxy-3-nitro-5-indanone (1.50 g, 7.80 mmol) and tin (II) chloride (5.25 g, 23.3 mmol) in ethanol(150 mL) was heated at 80° C. under argon. After 2 hours, the starting material had disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2Cl2) gave the desired product(1.00 g, 79%). 1H NMR (CD3OD): δ 6.85 (d,1H), 6.45 (d, 1H), 2.95 (d, 2H), 2.60 (d, 2H).

Workup

  1. temperatureto cool down
  2. additionpoured into ice
  3. extractionbefore being extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-f578a47543da4ff6819e42dfb7cb3346
Source dataset
uspto-grants-2001_01
Patent number
US06180675B2

Reaction notes

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