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

HRID 384798Notes

Reaction equation

HRID 384798 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]>[Pd].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, compound

Product 1

HCID 23033013Methyl 2-amino-4-(3-chloropropoxy)-5-methoxybenzoateYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a 50 mL volume glass flask equipped with a stirrer, a thermometer, a reflux condenser and a gas inlet 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, 0.46 g of 10 wt. % palladium/carbon and 16 mL of methanol. The resulting mixture was heated to 30° C. for 2 hours, while hydrogen was introduced to the mixture under atmospheric pressure at a rate of 50 mL/min. 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 0.85 g (reaction yield: 95.2%) of methyl 5-methoxy-4-(3-chloropropoxy)anthranilate.

Workup

  1. customIn a 50 mL volume glass flask equipped with a stirrer
  2. additionwas introduced to the mixture under atmospheric pressure at a rate of 50 mL/min
  3. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-139b0db2693c4eff8c7637c98ce2bb87
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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