Water → Ethyl 2-(2-methoxyanilino)benzoate

HRID 1249156Notes

Reaction equation

HRID 1249156 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:15](=O)[O:14][C:12](=[O:13])[C:11]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:10]12.[CH2:21]([Zn]CC)C.O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=1[C:12]([O:14][CH2:15][CH3:21])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 13424424HCID 13424424, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 13424425Ethyl 2-(2-methoxyanilino)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(2-Methoxyphenyl)isatoic anhydride (1 g, 0.00369 mole), 4 ml (0.00532 mole) of 1.33M diethylzinc in 4 ml of tetrahydrofuran, and 15 ml of tetrahydrofuran were combined at 0°-5° C. and then stirred at room temperature for two days. The reaction mixture was poured into water and extracted with ether. The ether extracts were washed with 20 ml of 1N potassium hydroxide, then dried over anhydrous magnesium sulfate and concentrated. The residue (1.12 g) was flash chromatographed on silica gel using 5% ethyl acetate/95% hexane as eluant to afford ethyl 2-(2-methoxyphenylamino)benzoate as a yellow viscous liquid, b.p. 284°-286° C. (760 mm).

Workup

  1. customwere combined at 0°-5° C.
  2. extractionextracted with ether
  3. washThe ether extracts were washed with 20 ml of 1N potassium hydroxide
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customchromatographed on silica gel using 5% ethyl acetate/95% hexane as eluant

Sources & evidence

ORD record
ord-5d5bd9ae2cea4440a34d8d4f287167d2
Source dataset
uspto-grants-1986_12
Patent number
US04629735

Reaction notes

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