Ammonium formate → HCID 18180252, compound

HRID 1359017Notes

Reaction equation

HRID 1359017 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[CH2:4][CH2:5][O:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([N+:15]([O-])=O)=[CH:9][C:8]=1[O:18][CH3:19])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH2:20]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[C:8]([O:18][CH3:19])=[CH:9][C:10]([NH2:15])=[CH:11][C:12]=1[O:13][CH3:14])[CH3:21]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18180274HCID 18180274, compound

Product 1

HCID 18180252HCID 18180252, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the nitro compound (440 mg, 1.48 mmol) in ethanol (15 ml) was added ammonium formate (600 mg, 9.45 mmol) and 10% Pd on carbon (100 mg) and the reaction stirred at room temperature for 18 h. The mixture was filtered through Celite™, the filtrate concentrated in vacuo and partitioned between ethyl acetate and water. The ethyl acetate layers were dried (MgSO4) and concentrated in vacuo to give 4-(2-diethylaminoethoxyl)-3,5-dimethoxy aniline as an orange powder (360 mg) δH (CDCl3) 5.92 (2H, s), 4.02 (2H, t, J 5.9 Hz), 3.77 (6H, s), 2.99 (2H, t, J 5.9 Hz), 2.80 (6H, m) and 1.11 (4H, t, J 6.9 Hz). MS (ES+) 269 (MH+, 100%).

Workup

  1. filtrationThe mixture was filtered through Celite™
  2. concentrationthe filtrate concentrated in vacuo
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe ethyl acetate layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8657c462d8c4524afd1f1a98df7306a
Source dataset
uspto-grants-2003_07
Patent number
US06599908B1

Reaction notes

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