Aniline → Methyl 4-(anilino)-2-(benzamido)benzoate

HRID 1673410Notes

Reaction equation

HRID 1673410 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].O1CCOCC1.[C:20]([NH:28][C:29]1[CH:38]=[C:37](Br)[CH:36]=[CH:35][C:30]=1[C:31]([O:33][CH3:34])=[O:32])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(O)(=O)C>[NH:1]([C:37]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[C:29]([NH:28][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:38]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 312751,4-DioxaneHCID 23676156Sodium t-butoxideHCID 57879335Methyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 57879357Methyl 4-(anilino)-2-(benzamido)benzoate

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 176Acetic AcidSolvent

Procedure

0.16 mL of aniline, 0.12 g of 1,1′-bis(diphenylphosphino)ferrocene, 0.057 g of (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride methylene chloride complex and 0.17 g of sodium tert-butoxide were added to 6 mL of dioxane solution containing 0.58 g of methyl 2-(benzamido)-4-bromobenzoate, and the resulting mixture was heated to reflux under nitrogen atmosphere for 4 hours. After the reaction mixture was cooled to room temperature, 1 mL of acetic acid was added and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to obtain 0.43 g of methyl 4-(anilino)-2-(benzamido)benzoate as colorless oil.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux under nitrogen atmosphere for 4 hours
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

Sources & evidence

ORD record
ord-fe756accc101483e848c841d7d5fcd42
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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