(3,4-Dimethoxyphenyl)acetic acid → HCID 12570797, compound

HRID 443734Notes

Reaction equation

HRID 443734 reaction equation
[NH2:1][C:2]([CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:6])([CH3:4])[CH3:3].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:23][C:24](O)=[O:25])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.O1CCCC1CCO>>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:23][C:24]([NH:1][C:2]([CH3:4])([CH3:3])[CH:5]([OH:6])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:25])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

5

Reactant 4

HCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 26760alpha-(1-Amino-1-methylethyl)benzenemethanolHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 119895722-(Oxolan-2-yl)ethan-1-ol

Product 1

HCID 12570797HCID 12570797, compoundYield 82%

Procedure

A solution of 8.3 g. (0.05 mole) of α-(1-amino-1-methylethyl)benzenemethanol, 9.8 g. (0.05 mole) of 3,4-dimethoxyphenylacetic acid and 13.6 g. (0.055 mole) of EEDQ (Aldrich Chem. Co.) in 300 ml. of tetrahydrofuran-ethanol is refluxed for 45 minutes and then allowed to stand for 20 hours at 25° C. The solution is evaporated in vacuo. The residue is taken up with 250 ml. of ethyl acetate, washed with dilute HCl, followed by washing with aqueous NaHCO3. Subsequently, the extract is washed with aqueous NaCl, dried (Na2SO4) and evaporated to dryness in vacuo. Crystallization of the residue from ether gives 14.0 g. (82% yield) of pure 2-(3,4-dimethoxyphenyl)-N-(β-hydroxy-α,α-dimethylphenethyl)acetamide, m.p. 123°-124° C.

Workup

  1. customThe solution is evaporated in vacuo
  2. washof ethyl acetate, washed with dilute HCl
  3. washby washing with aqueous NaHCO3
  4. washSubsequently, the extract is washed with aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness in vacuo
  7. customCrystallization of the residue from ether
  8. customgives 14.0 g

Sources & evidence

ORD record
ord-be27a9499e3c46a391df1b8fa8dbd5f3
Source dataset
uspto-grants-1981_04
Patent number
US04261890

Reaction notes

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