HCID 12071330, compound → HCID 23559778, compound

HRID 2301969Notes

Reaction equation

HRID 2301969 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([O:15]C)=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:17].B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([OH:15])=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:17]

Participants

4

Reactant 2

HCID 12071330HCID 12071330, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 23559778HCID 23559778, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of (7-methoxy-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl)-acetic acid methyl ester (5.4 g, 21.7 mmol) in 50 ml of methylene chloride at 0° C. was treated with 1.0 M BBr3—CH2Cl2 (200 ml, 200 mmol) under inert gas for 1 hour. The reaction mixture was allowed to warm to room temperature over an additional 2 hours. The volatiles were evaporated in vacuo to a brown oil which was treated with ice-cold methyl alcohol (400 ml×2) and evaporated after each treatment to a residue. The residue was refluxed with 5 ml of 12 N HCl and 100 ml of methyl alcohol for 2 hours and evaporated to a residue which was crystallized from methyl alcohol (25 ml) to give the title compound, (3.9 g) as fluffy tan needles, mp 178-179.5° C.

Workup

  1. customThe volatiles were evaporated in vacuo to a brown oil which
  2. additionwas treated with ice-cold methyl alcohol (400 ml×2)
  3. customevaporated after each treatment to a residue
  4. temperatureThe residue was refluxed with 5 ml of 12 N HCl and 100 ml of methyl alcohol for 2 hours
  5. customevaporated to a residue which
  6. customwas crystallized from methyl alcohol (25 ml)

Sources & evidence

ORD record
ord-62d013c16be3417493603d3ec84d64d4
Source dataset
uspto-grants-2002_08
Patent number
US06429214B1

Reaction notes

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