Hydrochloric Acid → 4-Aminoindane-5-carboxylic Acid

HRID 2353934Notes

Reaction equation

HRID 2353934 reaction equation
[OH:1]O.[NH:3]1[C:14]2[C:6](=[CH:7][CH:8]=[C:9]3[C:13]=2[CH2:12][CH2:11][CH2:10]3)[C:5](=[O:15])C1=O.[OH-].[Na+].Cl>O>[NH2:3][C:14]1[C:6]([C:5]([OH:15])=[O:1])=[CH:7][CH:8]=[C:9]2[C:13]=1[CH2:12][CH2:11][CH2:10]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 148855691,6,7,8-Tetrahydrocyclopenta[g]indole-2,3-dione

Product 1

HCID 148855494-Aminoindane-5-carboxylic AcidYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Add 30% aqueous hydrogen peroxide solution (5 mL) in water (44 mL) to a solution of 1,6,7,8-Tetrahydro-1-aza-as-indacene-2,3-dione (3.80 mg, 20.3 mmol) and sodium hydroxide (5.03 g, 126 mmol) in water (97 μL) over a period of 30 minutes, stir the mixture at room temperature for 1 h. Acidulate with 1N hydrochloric acid, filter the solid, wash with water and dry to afford 4-Amino-indan-5-carboxylic acid (3.13 g, 87%). Dissolve 4-Amino-indan-5-carboxylic acid (3.07 g, 17.3 mmol) in ethyl acetate (87 mL) and ethanol (87 mL) and add (trimethylsilyl) diazomethane (17.3 mL, 34.6 mmol, 2M in hexanes) at room temperature and stir the solution for 1 hour. Remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to afford the title compound (2.50 g, 76%). 1H NMR (MeOD, 300 MHz) δ 2.12 (quintuplet, J=7.6 Hz, 2H), 2.75 (t, J=7.5 Hz, 2H), 2.89 (t, J=7.5 Hz, 2H), 3.83 (s, 3H), 6.53 (d, J=8.1 Hz, 1H), 7.66 (d, J=8.1 Hz, 1H). MS (ES+): 192 (M+H).

Workup

  1. filtrationfilter the solid
  2. washwash with water
  3. customdry

Sources & evidence

ORD record
ord-79c2cd9c88ac42ac989cf85995fb0672
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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