Methanol → 1-Naphthylglycine methyl ester hydrochloride

HRID 1182407Notes

Reaction equation

HRID 1182407 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([NH:15][CH2:16][C:17]([OH:19])=[O:18])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.[CH3:20]O>C(OCC)C>[ClH:3].[CH3:20][O:18][C:17](=[O:19])[CH2:16][NH:15][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 4587031-Naphthylglycine

Product 1

HCID 668078681-Naphthylglycine methyl ester hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

33 mL of thionyl chloride was added dropwise to a mixture of 50.3 g of 1-naphthylglycine (racemic modification) and 200 mL of methanol (dehydrated) at an inner temperature of 35° C. over 1 hour and the mixture was stirred at the same temperature for 3 hours to effect reaction. The reaction mixture was concentrated and the concentrated residue obtained was mixed with 200 mL of diethyl ether. Then, the crystals produced were isolated by filtration and washed with 50 mL of diethyl ether. The crystals isolated by filtration were dried at an inner temperature of 50° C. under reduced pressure to obtain 61.9 g of ochre 1-naphthylglycine methyl ester hydrochloride (yield: 98%).

Workup

  1. customreaction
  2. concentrationThe reaction mixture was concentrated
  3. customthe concentrated residue obtained
  4. customThen, the crystals produced
  5. customwere isolated by filtration
  6. washwashed with 50 mL of diethyl ether
  7. customThe crystals isolated by filtration
  8. customwere dried at an inner temperature of 50° C. under reduced pressure

Sources & evidence

ORD record
ord-5ebf12c3bd4848138bcd2727dc20ceb5
Source dataset
uspto-grants-2007_10
Patent number
US07288674B2

Reaction notes

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