Hydrochloric Acid → 4-Aminoindane-5-carboxylic Acid

HRID 507065Notes

Reaction equation

HRID 507065 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 NaOH (5.03 g, 126 mmol) in water (97 mL) 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, 2 M in hexanes) at room temperature and stir the solution for 1 h. 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-020b270d1c4e46a997b2d26b65fa4b5d
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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