Hydrochloric Acid → 6-amino-2,3-dihydro-1H-indene-5-carboxylic acid

HRID 507074Notes

Reaction equation

HRID 507074 reaction equation
[OH:1]O.[NH:3]1[C:14]2[C:6](=[CH:7][C:8]3[CH2:9][CH2:10][CH2:11][C:12]=3[CH:13]=2)[C:5](=[O:15])C1=O.Cl>[OH-].[Na+]>[NH2:3][C:14]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][C:6]=1[C:5]([OH:15])=[O:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 22560824Cyclopent[f]indole-2,3-dione, 1,5,6,7-tetrahydro-

Product 1

HCID 227442886-amino-2,3-dihydro-1H-indene-5-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Add 30% aqueous hydrogen peroxide solution (3 mL) to a solution of 1,5,6,7-tetrahydro-1-aza-s-indacene-2,3-dione (2.18 g, 11.66 mmol) in 2 N NaOH (23 mL) over a period of 5 minutes, stir the mixture at room temperature for 3 h. Add 1N hydrochloric acid to pH=5 and extract with ethyl acetate (3×20 mL). Wash with brine, dry the organic layer over anhydrous sodium sulfate, filter and remove the solvent under reduced pressure to afford 6-amino-indan-5-carboxylic acid (1.7 g, 86%). Dissolve in ethyl acetate (2 mL) and ethanol (2 mL) and add (trimethylsilyl) diazomethane (9.6 mL, 19.2 mmol, 2 M in hexane) at room temperature and stir the solution for 16 h. Remove the solvent under reduced pressure. Chromatograph the residue over silica gel, eluting with hexanes/ethyl acetate (9:1), to afford the title compound (1.19 g, 66%). 1H NMR (CDCl3, 300 MHz) δ 2.05 (quintuplet, J=7.3 Hz, 2H), 2.80 (q, J=7.7 Hz, 4H), 6.59 (s, 1H), 7.69 (s, 1H). MS (ES+): 192 (M+H).

Workup

  1. extractionextract with ethyl acetate (3×20 mL)
  2. washWash with brine
  3. dry with materialdry the organic layer over anhydrous sodium sulfate
  4. filtrationfilter
  5. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-5add983a6f21476dafb9e53233d08741
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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