HCID 67119435, compound → HCID 67119420, compound

HRID 384833Notes

Reaction equation

HRID 384833 reaction equation
[CH3:1][C:2]1[C:13]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)=[CH:12][C:5]([C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[O:7])=[C:4]([N+:26]([O-])=O)[CH:3]=1>[C].[Pd].CO>[NH2:26][C:4]1[CH:3]=[C:2]([CH3:1])[C:13]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:23])([F:24])[F:25])=[CH:17][CH:16]=2)=[CH:12][C:5]=1[C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[O:7]

Participants

4

Reactant 1

HCID 67119435HCID 67119435, compound

Product 1

HCID 67119420HCID 67119420, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

An 80% methanol (225 g), 50 g of isopropyl 4-methyl-2-nitro-5-(4-(trifluoromethoxy)phenoxy)benzoate, and 2.5 g of a 5% palladium carbon were charged into a 500-ml stainless steel autoclave equipped with a stirring device and a thermometer, and a reaction was allowed to proceed under a hydrogen pressure of 0.5 MPa at 30° C. for 6 hr. After the replacement of the air in the autoclave with nitrogen, the reaction solution was filtered using 220 ml of methanol to remove the catalyst. The methanol solution thus obtained was concentrated under the reduced pressure, and 208 ml of water was added to the residue. The precipitated solid was collected by filtration and was dried to give isopropyl 2-amino-4-methyl-5-(4-(trifluoromethoxy)phenoxy)benzoate (43.96 g, yield: 95%).

Workup

  1. customequipped with a stirring device
  2. customat 30° C.
  3. customfor 6 hr
  4. filtrationAfter the replacement of the air in the autoclave with nitrogen, the reaction solution was filtered
  5. customto remove the catalyst
  6. customThe methanol solution thus obtained
  7. concentrationwas concentrated under the reduced pressure, and 208 ml of water
  8. additionwas added to the residue
  9. filtrationThe precipitated solid was collected by filtration
  10. customwas dried

Sources & evidence

ORD record
ord-49bf7e32d61f4c0bbe843588ff6d2726
Source dataset
uspto-grants-2013_02
Patent number
US08367833B2

Reaction notes

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