Hydrochloric Acid → 5-Methoxy-3-methoxycarbonylmethyl-indan-1-yl-ammonium chloride

HRID 536636Notes

Reaction equation

HRID 536636 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7](=[N:16]O)[CH2:6]1.[ClH:19]>[Pd].CO>[Cl-:19].[CH3:15][O:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]([NH3+:16])[CH2:6][CH:5]2[CH2:4][C:3]([O:2][CH3:1])=[O:18]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86650493(3-Hydroxyimino-6-methoxy-indan-1-yl)-acetic acid methyl ester

Product 1

HCID 866562075-Methoxy-3-methoxycarbonylmethyl-indan-1-yl-ammonium chloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 10% palladium on carbon (3.0 g), (3-hydroxyimino-6-methoxy-indan-1-yl)-acetic acid methyl ester (12.5 g), and concentrated hydrochloric acid (4.7 mL) in methanol (150 mL) is stirred under hydrogen atmosphere at room temperature overnight. The mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is azeotropically dried using toluene and washed with diisopropylether to give the product as a white solid after drying at 50° C.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is azeotropically dried
  4. washwashed with diisopropylether

Sources & evidence

ORD record
ord-8c65e05a468e4c91a5f8a0a309f50f68
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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