Ammonia → AC-7739 free base

HRID 585320Notes

Reaction equation

HRID 585320 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]\[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([N+:23]([O-])=O)[CH:16]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C([O-])=O.[NH4+].N>C(#N)C.[Pt]>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15](/[CH:14]=[CH:13]\[C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:16][C:17]=1[NH2:23]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 2723923Ammonium formateHCID 10617491(Z)-1,2,3-trimethoxy-5-(4-methoxy-3-nitrostyryl)benzene4×

Product 1

HCID 9796936AC-7739 free base

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution was prepared by dissolving (Z)-3,4,4′,5-tetramethoxy-3′-nitrostilbene (raw material 5) (8.63 g, 25.0 mmol) in acetonitrile (100 ml) succeeded by addition of ammonium formate (5.21 g, 82.6 mmol, 330 mole % to the above nitrostilbene derivative (raw material 5)), 5% platinum on carbon (water-content: 60.91%, 4.99 g, 0.50 mmol as platinum) and aqueous ammonia (28%, 1.69 ml, 25 mmol) to be reacted at 30° C. for 23 hours in an argon atmosphere. At the conclusion of the reaction, the catalyst and the insoluble matter were separated by filtration and the filtrate was subjected to quantitative analysis by HPLC. Formation of the objective substance, (Z)-2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)vinyl]aniline (objective substance 6; represented by the above formula (6)) (6.52 g, 20.7 mmol, 83%), was confirmed, as was formation of a by-product (E)-2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)vinyl]aniline (by-product 7; represented by the above formula (7)) (0.55 g, 1.73 mmol, 6.9%) and a by-product 2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethyl]aniline (by-product 8; represented by the above formula (8)) (0.52 g, 1.63 mmol, 6.5%). Formation was not observed for the by-product 2-(4-methoxy-3-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)ethane (by-product 9; represented by the above formula (9)).

Workup

  1. customA solution was prepared
  2. customto be reacted at 30° C. for 23 hours in an argon atmosphere
  3. customAt the conclusion of the reaction
  4. customthe catalyst and the insoluble matter were separated by filtration

Sources & evidence

ORD record
ord-dbd70ad045dc44e687c142c770399901
Source dataset
uspto-grants-2005_08
Patent number
US06930205B2

Reaction notes

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