3-Chloroaniline → (E)-3-(4-((3-Chlorophenylamino)methyl)phenyl)acrylic acid

HRID 252846Notes

Reaction equation

HRID 252846 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1)=O.[Cl:14][C:15]1[CH:16]=[C:17]([NH2:21])[CH:18]=[CH:19][CH:20]=1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1.CO>[Cl:14][C:15]1[CH:16]=[C:17]([NH:21][CH2:1][C:3]2[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=2)[CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 79323-ChloroanilineHCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 5357280p-Formylcinnamic acid

Product 1

HCID 59736746(E)-3-(4-((3-Chlorophenylamino)methyl)phenyl)acrylic acidYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-3-(4-formylphenyl)acrylic acid 229 (1 g, 5.67 mmol) and 3-chlorobenzenamine 230 (596 L, 5.67 mmol) in THF (8 ml), dibutyltin dichloride (173 mg, 0.57 mmol) was added followed by dropwise addition of phenylsilane (697 uL, 5.67 mmol). The resulting mixture was stirred at room temperature in the nitrogen atmosphere overnight, diluted with MeOH and concentrated under reduced pressure. The solid residue was triturated with DCM to yield the title compound 231 (1.24 g, 76% yield). 1H NMR: (DMSO) δ (ppm): 7.61 (d, J=8.0 Hz, 2H), 7.53 (d, J=16.0 Hz, 1H), 7.34 (d, J=8.4 Hz, 2H), 7.00 (t, J=8.0 Hz, 1H), 6.53 (t, J=2.0 Hz, 1H), 6.49-6.48 (m, 2H), 6.46 (d, J=16.0 Hz, 1H), 4.28 (bs, 2H). MS: (calc.) 287.7; (obt.) 288.1 (MH)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe solid residue was triturated with DCM

Sources & evidence

ORD record
ord-250c94dad27d4b2e9bbd96083bfb12cf
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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