Sodium Hydroxide → [2-[(3-Amino-2-pyridinyl)[3-(dimethylamino)propyl]amino]phenyl]phenylmethanone

HRID 1633361Notes

Reaction equation

HRID 1633361 reaction equation
[CH3:1][N:2]([CH3:30])[CH2:3][CH2:4][CH2:5][N:6]([C:21]1[C:26]([N+:27]([O-])=O)=[CH:25][CH:24]=[CH:23][N:22]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14].[OH-].[Na+]>C(O)C.O.[Zn]>[CH3:30][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]([C:21]1[C:26]([NH2:27])=[CH:25][CH:24]=[CH:23][N:22]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:14]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 54525496[2-[[3-(Dimethylamino)propyl](3-nitro-2-pyridinyl)amino]phenyl]phenylmethanone

Product 1

HCID 53769600[2-[(3-Amino-2-pyridinyl)[3-(dimethylamino)propyl]amino]phenyl]phenylmethanone

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of (0.05 mole) [2-[[3-(dimethylamino)propyl](3-nitro-2-pyridinyl)amino]phenyl]phenylmethanone, 13 g, (0.20 mole) of zinc dust, 2 g (0.05 mole) of sodium hydroxide in 75 ml ethanol and 25 ml water is stirred under reflux for 1 hr. The mixture is filtered and evaporated under reduced pressure. The residue is dissolved in methylene chloride and the resulting solution is dried over magnesium sulfate and decolorized with charcoal and filtered. The filtrate is evaporated to dryness to give the title compound in crude mixture.

Workup

  1. temperatureunder reflux for 1 hr
  2. filtrationThe mixture is filtered
  3. customevaporated under reduced pressure
  4. dissolutionThe residue is dissolved in methylene chloride
  5. dry with materialthe resulting solution is dried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-e69fcdefcfb34d339ecbb4db21f4cb1c
Source dataset
uspto-grants-1984_10
Patent number
US04480100

Reaction notes

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