HCID 17989424, compound → HCID 69422920, compound

HRID 1353091Notes

Reaction equation

HRID 1353091 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[CH2:11][CH2:10][CH2:9]1>C1COCC1.C(O)C.[Pd]>[N:8]1([CH2:7][CH2:6][O:5][C:4]2[CH:12]=[CH:13][C:14]([NH2:16])=[CH:15][C:3]=2[O:2][CH3:1])[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 1

HCID 17989424HCID 17989424, compound

Product 1

HCID 69422920HCID 69422920, compoundYield 100.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-[2-(2-methoxy-4-nitro-phenoxy)-ethyl]-azetidine (53.5 mg, 0.21 mmol) was dissolved in a 1:1 mixture of THF and ethanol (7 ml) and 10% palladium on carbon paste (150 mg) introduced. The reaction mixture was stirred under an atmosphere of hydrogen for 50 hours at RT. The catalyst was filtered off over filter-aid and the filtrate evaporated to give 4-[2-azetidin-1-yl-ethoxy]-3-methoxy-phenylamine as a brown oil (47 mg, 100%). This material was treated with 3-phenoxyphthalic anhydride in the same manner as for 4-(2-diisopropylamino-ethoxy)-3-methoxy-phenylamine in Example A4 to give the title compound.

Workup

  1. additionintroduced
  2. filtrationThe catalyst was filtered off
  3. filtrationover filter-aid
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-4df76effb5ab463bb998e34fc6f88a93
Source dataset
uspto-grants-2007_05
Patent number
US07220777B2

Reaction notes

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