Hydrochloric Acid → HCID 19995504, compound

HRID 2249025Notes

Reaction equation

HRID 2249025 reaction equation
COC1C(OC)=CC=C2C=1CCC2=O.C(ON=O)CCC.[ClH:22].[CH3:23][O:24][C:25]1[C:33]([O:34][CH3:35])=[CH:32][CH:31]=[C:30]2[C:26]=1[CH2:27][C:28](=[N:37]O)[C:29]2=O>CO>[ClH:22].[CH3:23][O:24][C:25]1[C:33]([O:34][CH3:35])=[CH:32][CH:31]=[C:30]2[C:26]=1[CH2:27][CH:28]([NH2:37])[CH2:29]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10996Butyl nitriteHCID 2404464,5-Dimethoxy-1-indanoneHCID 73669108HCID 73669108, compound

Product 1

HCID 19995504HCID 19995504, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a procedure described by Cannon, J. G. et al. in J. Med. Chem., V.25, p. 1442 (1982), 4, 5-dimethoxy-1-indanone is reacted with n-butylnitrite in methanol and upon acidification with HCl, 4,5-dimethoxy-2-oximino-1-indanone is recovered as a precipitate. This is added to a major amount of glacial acetic acid and a minor amount of concentrated sulfuric acid and hydrogenated over a palladium on carbon catalyst to produce 4,5-dimethoxy-2-aminoindan hydrochloride, which is then recovered.

Workup

  1. customis recovered as a precipitate
  2. additionThis is added to a major amount of glacial acetic acid

Sources & evidence

ORD record
ord-03c6b8f7372540faa4ba04d8f5d96565
Source dataset
uspto-grants-1991_08
Patent number
US05041669

Reaction notes

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