Hydrochloric Acid → 3-Chloro-4-(methoxycarbonyl)benzoic acid

HRID 924994Notes

Reaction equation

HRID 924994 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=[O:6].N([O-])=O.[Na+].CCOC(C)=O.[ClH:25]>C(O)(=O)C.Cl[Cu]>[Cl:25][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8857Ethyl AcetateHCID 52355003-Amino-4-(methoxycarbonyl)benzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 143722353-Chloro-4-(methoxycarbonyl)benzoic acidYield 93%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolvent

Procedure

To a mixture of 3-amino-4-(methoxycarbonyl)benzoic acid (781 mg, 4.0 mmol) suspended in acetic acid (10 mL) and conc. HCl (10 mL) was added aq. NaNO2 (276 mg, 4.0 mmol, 5 mL) at 0° C. The resulting mixture was stirred for 30 minutes. CuCl (400 mg, 8.0 mmol) in 10 mL of conc. HCl. was added to the mixture at 0° C. The resulting mixture was stirred at 30° C. for 6 hours. Followed a standard aqueous/EtOAc workup procedure (800 mg, yield 93%).

Workup

  1. additionwas added to the mixture at 0° C
  2. stirringThe resulting mixture was stirred at 30° C. for 6 hours

Sources & evidence

ORD record
ord-998d043d9c634784a80f85d83212796a
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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