Sodium Hydroxide → HCID 86008622, compound

HRID 1660989Notes

Reaction equation

HRID 1660989 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-])=O)=[CH:12][CH:13]=2)[C:8](=[O:18])[CH2:7]1)=[O:5])[CH3:2].[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]([CH:6]1[C:14]2[C:9](=[CH:10][C:11]([NH2:15])=[CH:12][CH:13]=2)[C:8](=[O:18])[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 85855183HCID 85855183, compound

Product 1

HCID 86008622HCID 86008622, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R/S)-5-Nitro-3-oxo-indan-1-carboxylic acid ethyl ester (3 g, 12 mmol) (Gadient, Fulvio; Suess, Rudolf. Indane carboxylic acids, DE 2505447) is added portionwise over 5 minutes to a stirred suspension of tin (II) chloride (13.9 g, 60.2 mmol) in ethanol (50 mL) at rt under nitrogen. The reaction is then refluxed for 30 min, cooled to rt, poured into ice water and the pH adjusted to 9 with 1M sodium hydroxide. The mixture is extracted with diethyl ether and then washed with brine, dried and concentrated in vacuo to give (R/S)-5-amino-3-oxo-indan-1-carboxylic acid ethyl ester as a light yellow solid. Title compound: ES-MS: 219.96 [M+H]+; tR=0.8 min (System 2).

Workup

  1. temperatureThe reaction is then refluxed for 30 min
  2. extractionThe mixture is extracted with diethyl ether
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad8e3b08ec824bb2a11aca10ce5a9b9d
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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