Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate → Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate

HRID 1094537Notes

Reaction equation

HRID 1094537 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:16]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([N+:22]([O-])=O)[CH:7]=1.[H][H]>[Pt].CO>[NH2:22][C:8]1[CH:7]=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[C:16]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 11186961Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 11347513Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoateYield 92.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

In a 20 L-volume glass reaction vessel equipped with a stirrer, a thermometer and a reflux condenser, 2,328 g (6.78 moles) of the ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate prepared in the Synthesis Example 2, 2 wt. % platinum per 118 g of carbon (50 wt. % product, N.E. Chemcat Corporation, 6.0 mmoles in terms of platinum metallic atom) and 9,440 mL of methanol were placed. The mixture was allowed to react at 50 to 60° C. for 6 hours in an atmosphere of hydrogen while stirring. After the reaction was complete, the reaction solution was cooled to room temperature, and filtered. The filtrate was concentrated under reduced pressure to obtain 1,960 g of ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate as an orange liquid (isolation yield: 92%).

Workup

  1. customIn a 20 L-volume glass reaction vessel
  2. customequipped with a stirrer
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f1a3e4bcad04401496ea4420c2c479ca
Source dataset
uspto-grants-2012_03
Patent number
US08133999B2

Reaction notes

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