5-Bromo-2-chloro-1-(4-methoxycarbonyl-5-oxazolylmethyl)benzene → 1-(3-Amino-2-oxopropyl)-5-bromo-2-chlorobenzene-hydro-chloride

HRID 1625888Notes

Reaction equation

HRID 1625888 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:18])=[C:6]([CH2:8][C:9]2[O:13]C=[N:11][C:10]=2C(OC)=O)[CH:7]=1>Cl>[ClH:18].[NH2:11][CH2:10][C:9](=[O:13])[CH2:8][C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[Cl:18]

Participants

3

Reactant 1

HCID 666081825-Bromo-2-chloro-1-(4-methoxycarbonyl-5-oxazolylmethyl)benzene

Product 1

HCID 666088101-(3-Amino-2-oxopropyl)-5-bromo-2-chlorobenzene-hydro-chlorideYield 279.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The above 5-bromo-2-chloro-1-(4-methoxycarbonyl-5-oxazolylmethyl)benzene (1.37 g) was heated under reflux in 6N aqueous hydrochloric acid solution (20 ml) overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in methanol, and treated with carbon powder. The carbon powder was filtered off, and the filtrate was evaporated under reduced pressure to give crude 1-(3-amino-2-oxopropyl)-5-bromo-2-chlorobenzene.hydrochloride (1.73 g) as a pale brown solid, which was used in the subsequent step without further purification. APCI-Mass m/Z 262/264 (M+H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in methanol
  3. additiontreated with carbon powder
  4. filtrationThe carbon powder was filtered off
  5. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-59cf1ac6004347c18b62a7ad287af3e1
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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