Acetic Acid → HCID 67199091, compound

HRID 1948731Notes

Reaction equation

HRID 1948731 reaction equation
[NH2:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.C(O)(=O)C.[C:16](OC)(=[O:22])[CH2:17][C:18]([O:20][CH3:21])=[O:19].N1CCCCC1>C1(C)C=CC=CC=1.O>[CH3:21][O:20][C:18]([C:17]1[C:16](=[O:22])[NH:1][C:2]2[C:3]([CH:4]=1)=[CH:6][CH:7]=[CH:8][C:9]=2[O:10][CH3:11])=[O:19]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7943Dimethyl malonateHCID 8082PiperidineHCID 139701212-Amino-3-methoxybenzaldehyde

Product 1

HCID 67199091HCID 67199091, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution/suspension of 2-amino-3-methoxybenzaldehyde (1.8 g, 11.9 mmol) in dry toluene (30 mL) under nitrogen was added acetic acid (0.1 mL) followed by dimethyl malonate (3.4 mL, 29.8 mmol) and piperidine (2.9 mL, 29.8 mmol). The reaction mixture was heated at reflux for 2 h. After cooling to r.t., the mixture was diluted with water (30 mL) and extracted with EtOAc (2×150 mL). The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo. The residue was triturated in EtOAc/Et2O and the resulting solid was filtered off and dried in vacuo to give the title compound (1.7 g, 61%) as a pale yellow solid. δH (DMSO-d6) 10.65 (br s, 1H), 8.52 (s, 1H), 7.42 (d, J 8.0 Hz, 1H), 7.27 (d, J 8.0 Hz, 1H), 7.21 (t, J 6.0 Hz, 1H), 3.94 (s, 3H), 3.84 (s, 3H). LCMS (ES+) 234 (M+H)+, RT 2.13 minutes (Method 5).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. extractionextracted with EtOAc (2×150 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated in EtOAc/Et2O
  9. filtrationthe resulting solid was filtered off
  10. customdried in vacuo

Sources & evidence

ORD record
ord-bf60c2d96d68471588977af39a5a5371
Source dataset
uspto-grants-2013_03
Patent number
US08399483B2

Reaction notes

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