Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate → Methyl 2-amino-4-(3-chloropropoxy)-5-methoxybenzoate

HRID 384797Notes

Reaction equation

HRID 384797 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:16][CH2:17][CH2:18][CH2:19][Cl:20])=[CH:5][C:6]([N+:13]([O-])=O)=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9]>[Ni].C(O)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:6]([NH2:13])=[CH:5][C:4]=1[O:16][CH2:17][CH2:18][CH2:19][Cl:20]

Participants

4

Reactant 1

HCID 23032992Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate

Product 1

HCID 23033013Methyl 2-amino-4-(3-chloropropoxy)-5-methoxybenzoateYield 85.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 284Formic AcidSolvent

Procedure

In a 50 mL volume glass flask equipped with a stirrer, a thermometer and a reflux condenser were placed 1.01 g (3.29 mmol) of methyl 5-methoxy-4-(3-chloropropoxy)-2-nitrobenzoate (purity: 99%) obtained in Reference Example III-4, 1.0 g of a developed Raney nickel, and 10 mL of formic acid. The reaction was carried out at 70° C. for 8 hours. After the reaction was complete, the reaction mixture was filtered. The filtrate was analyzed by high performance liquid chromatography (absolute quantitative analysis). There was produced 0.77 g (reaction yield: 85.0%) of methyl 5-methoxy-4-(3-chloropropoxy)-anthranilate.

Workup

  1. customIn a 50 mL volume glass flask equipped with a stirrer
  2. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-181afd7d247b444687a4ef5d1c6bf867
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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