HCID 66811667, compound → HCID 66812127, compound

HRID 1097851Notes

Reaction equation

HRID 1097851 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[C:8]([N+:20]([O-])=O)[CH:7]=1>C(O)(=O)C.[Sn](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:23])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][CH2:14][N:15]([CH2:16][CH3:17])[CH2:18][CH3:19])=[C:8]([NH2:20])[CH:7]=1

Participants

4

Reactant 1

HCID 66811667HCID 66811667, compound

Product 1

HCID 66812127HCID 66812127, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 24287Tin tetrachlorideSolvent

Conditions

Temperature
45 °C

Procedure

To a pre-stirred solution of 3-[4-(2-diethylamino-ethylamino)-3-nitro-phenyl]-acrylic acid methyl ester (61-1, 280 mg, 1.0 mmol) in glacial acetic acid (5 mL), tin chloride was added (1.18 g, 10.0 mmol). The resulting solution was heated to 45° C. for 17 hours and then cooled to room temperature. The solvent was removed under vacuum. Water (20 mL) and dichloromethane (20 mL) was added to the residue and stirred for 30 minutes. The organic layer was dried (MgSO4), filtered and concentrated to an oily residue. 100 mL diethyl ether was added and stirred for 4 hours. The product 3-[3-amino-4-(2-diethylamino-ethylamino)-phenyl]-acrylic acid methyl ester was obtained in 54.9% yield (207.6 mg). LCMS m/z: 292 ([M+H]+).

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent was removed under vacuum
  3. additionWater (20 mL) and dichloromethane (20 mL) was added to the residue
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to an oily residue
  7. addition100 mL diethyl ether was added
  8. stirringstirred for 4 hours

Sources & evidence

ORD record
ord-7abdfe0479424ed8a77113bf3a83842c
Source dataset
uspto-grants-2012_03
Patent number
US08143282B2

Reaction notes

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