Ammonium formate → 4-[2-(Oxan-2-yloxy)ethoxy]aniline

HRID 2170535Notes

Reaction equation

HRID 2170535 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)=[CH:6][CH:5]=1)([O-])=O.C([O-])=O.[NH4+]>CCO.[Pd]>[O:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH:14]1[O:13][CH2:12][CH2:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 108908362-[2-(4-Nitrophenoxy)ethoxy]oxane2×

Product 1

HCID 110209174-[2-(Oxan-2-yloxy)ethoxy]aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-({2-[(4-nitrophenyl)oxy]ethyl}oxy)tetrahydro-2H-pyran (Intermediate 17) (1.33 g, 5 mmol) in EtOH (50 mL) was added Pd/C (catalytic amount) and ammonium formiate (0.9 g, 10 eq). The reaction was stirred to 40° C. for 2 hours. After filtration on celite, the solvent was evaporated and the residue was poured in water, extracted with ether and dried over sodium sulphate and evaporated. The title compound was obtained as a dark oil (0.8 g, 68%). LC/MS: m/z 238 (M+H)+, Rt: 2.38 min.

Workup

  1. filtrationAfter filtration on celite
  2. customthe solvent was evaporated
  3. additionthe residue was poured in water
  4. extractionextracted with ether
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-381e90b114034db6a55c7486c9cdb8d4
Source dataset
uspto-grants-2015_06
Patent number
US09051281B2

Reaction notes

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