Hydrochloric Acid → HCID 11075774, compound

HRID 725919Notes

Reaction equation

HRID 725919 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][CH:7]([NH2:14])[CH2:6]2.C(=O)([O-])[O-].[Na+].[Na+].Cl>CN(C)C=O.C(#N)C.C(OCC)(=O)C>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[CH2:6][CH:7]([N:14]1[CH2:10][CH2:11][CH2:3][CH2:4]1)[CH2:8]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 110416235,6-dimethoxy-2,3-dihydro-1H-inden-2-amine

Product 1

HCID 11075774HCID 11075774, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5,6-dimethoxy-2-aminoindan (Preparation 5, 4.5 mmol) in dimethylformamide/acetonitrile (1:6, 49 mL) was added sodium carbonate (1.43 g, 13.5 mmol) and was heated (100° C.) overnight. The mixture was diluted with ethyl acetate, filtered and the filtrate concentrated. The oily residue was chromatographed (400 g silica gel) eluting with methylene chloride/methanol (9:1) to yield a yellow oil. The oil was converted into the HCl salt and recrystallized from methanol/ethyl acetate: mp 267°-269° C.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated
  3. customThe oily residue was chromatographed (400 g silica gel)
  4. washeluting with methylene chloride/methanol (9:1)
  5. customto yield a yellow oil
  6. customrecrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-9781a44935ff4ade8a1656b116b13ebb
Source dataset
uspto-grants-1998_01
Patent number
US05708018

Reaction notes

Loading…