Aluminum(III) Chloride → Methyl 5-aminoindane-4-carboxylate

HRID 604618Notes

Reaction equation

HRID 604618 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].C(OC([NH:11][C:12]1[CH:20]=[CH:19][C:18]2[CH2:17][CH2:16][CH2:15][C:14]=2[C:13]=1[C:21]([O:23][CH3:24])=[O:22])=O)(C)C>C1(C)C=CC=CC=1>[NH2:11][C:12]1[CH:20]=[CH:19][C:18]2[CH2:17][CH2:16][CH2:15][C:14]=2[C:13]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 67057713Methyl 5-[(isopropoxycarbonyl)amino]indane-4-carboxylate

Product 1

HCID 67057733Methyl 5-aminoindane-4-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Aluminium trichloride (146 mg, 1.09 mmol) was added to dry toluene (2 mL) at 0° C. Methyl 5-[(isopropoxycarbonyl)amino]indane-4-carboxylate (76 mg, 0.274 mmol) was added portionwise as a powder to the mixture above. The thick suspension was stirred at room temperature for 15 min and heated at 80° C. for 6 h. The mixture was poured into ice water and extracted with EtOAc (3×). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to afford methyl 5-aminoindane-4-carboxylate. LCMS calc.=192.1; found=192.2 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 7.14 (d, J=8.1 Hz, 1H); 6.55 (d, J=8.1 Hz, 1H); 3.88 (s, 3H); 3.17 (t, J=7.5 Hz, 2H); 2.82 (t, J=7.5 Hz, 2H); 2.05-1.98 (m, 2H).

Workup

  1. temperatureheated at 80° C. for 6 h
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-804cd7278881452f98583862505c4dfd
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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