3-Methoxyaniline → HCID 54704900, compound

HRID 751320Notes

Reaction equation

HRID 751320 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.[C:10]1([CH:16]([C:22](OCC)=[O:23])[C:17](OCC)=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[C:10]1([C:16]2[C:17](=[O:18])[NH:9][C:5]3[C:6]([C:22]=2[OH:23])=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 108243-MethoxyanilineHCID 66514Diethyl phenylmalonate

Product 1

HCID 54704900HCID 54704900, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A dark solution of 3-anisidine (5.37 g, 44.8 mmol), diethyl 2-phenylmalonate (10.57 g, 44.8 mmol), and diphenyl ether (50 mL) was heated at 220° C. for 1 h without a reflux condenser to allow ethanol evaporation. The reaction was cooled to rt, and the resultant gray precipitate filtered and washed with diethyl ether and dried to afford 11.0 g 2a (R2=7-OMe in Scheme 1, 92% yield): MS (M+H)+ 269.28.

Workup

  1. customethanol evaporation
  2. filtrationthe resultant gray precipitate filtered
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-ff0585c6fe2342919410f7ae8bee4e25
Source dataset
uspto-grants-2008_07
Patent number
US07405303B2

Reaction notes

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