Hydrochloric Acid → HCID 12109165, compound

HRID 1274176Notes

Reaction equation

HRID 1274176 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C@H:12]([NH:14][C:15](=[O:17])[CH3:16])[CH3:13])[C:5]([O:7][CH3:8])=[O:6].N([O-])=O.[Na+].[ClH:22]>C(O)(=O)C.S(=O)(=O)(O)O.[Cu]Cl>[C:15]([NH:14][C@@H:12]([C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[Cl:22])[CH3:13])(=[O:17])[CH3:16]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 12109152HCID 12109152, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 12109165HCID 12109165, compound

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of methyl (R)-3-amino-4-(1-acetamidoethyl)benzoate (600 mg) in acetic acid (6 ml) was dropwise added to a solution of sodium nitrite (193mg) in conc. sulfuric acid (2 ml) at room temperature, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was dropwise added to a solution of copper(I) chloride (550 mg) in conc. hydrochloric acid (6 ml) under ice-cooling, and the mixture was stirred at room temperature for 5 hours. After the reaction, the reaction mixture was poured into ice water, dried, and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to give 460 mg of methyl (R)-4-(1-acetamidoethyl)-3-chlorobenzoate.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 5 hours
  3. customAfter the reaction
  4. customdried
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-f7c0d34e17dd413aa340fd09c2883018
Source dataset
uspto-grants-2000_12
Patent number
US06156766

Reaction notes

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