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

HRID 2353926Notes

Reaction equation

HRID 2353926 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 sodium hydroxide (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 ethylacetate (2 mL) and ethanol (2 mL) and add (trimethylsilyl) diazomethane (9.6 mL, 19.2 mmol, 2M 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-53bc663b7dcb448c84f64624438e6df0
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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