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

HRID 384794Notes

Reaction equation

HRID 384794 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].[H][H]>[Ni].CO>[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

5

Reactant 2

HCID 23032992Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 23033013Methyl 2-amino-4-(3-chloropropoxy)-5-methoxybenzoateYield 95%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In a 50 mL volume pressure-resistant vessel were placed 2.02 g (6.58 mmol) of methyl 5-methoxy-4-(3-chloropropoxy)-2-nitrobenzoate (purity: 99%) obtained in Reference Example III-4, 2.0 g of a developed Raney nickel, and 40 mL of methanol. The atmosphere in the vessel was replaced with hydrogen, and the vessel was closed. The reaction was carried out at 90-100° C. for 24 hours at a hydrogen pressure of 0.9 MPa (gauge pressure). 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 1.71 g (reaction yield: 95.0%) of methyl 5-methoxy-4-(3-chloropropoxy)anthranilate.

Workup

  1. customIn a 50 mL volume pressure-resistant vessel were placed
  2. customthe vessel was closed
  3. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-4d6f71986aae4c74a1b01ae934867e7a
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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