3-Methoxybenzaldehyde → HCID 135939084, compound

HRID 591865Notes

Reaction equation

HRID 591865 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O.OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1.O>CC(N(C)C)=O.CCOC(C)=O>[CH3:14][O:13][C:7]1[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:2]2[C:3]=1[C:4](=[O:5])[NH:6][C:20]([C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([O:16][CH3:15])[CH:18]=1)=[N:1]2

Participants

7

Reactant 4

HCID 115693-MethoxybenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 23665763Sodium Bisulfite

Product 1

HCID 135939084HCID 135939084, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-amino-4,6-dimethoxybenzamide (0.0600 g, 0.306 mmol), 3-methoxybenzaldehyde (0.306 mmol), NaHSO3 (94%, 0.0474 g, 0.428 mmol), and p-TsOH.H2O (0.0175 g, 0.0918 mmol) in DMA (3.06 mL) was heated at 140° C. for 20 hours. The mixture was diluted with EtOAc (300 mL), washed with water (3×75 mL), then brine (75 mL), dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was purified on silica gel (40 g, CH2Cl2/MeOH) and the product was freeze-dried from MeCN/H2O to provide the title compound (69%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6): δ 12.04 (s, 1H), 7.82-7.70 (m, 2H), 7.43 (t, J=7.98 Hz, 1H), 7.13 (dd, J=8.19, 2.46 Hz, 1H), 6.76 (d, J=2.19 Hz, 1H), 6.55 (d, J=2.19 Hz, 1H), 3.92-3.82 (m, 9H); MS (APCI) m/z 313 [C17H16N2O4+H]+.

Workup

  1. washwashed with water (3×75 mL)
  2. dry with materialbrine (75 mL), dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified on silica gel (40 g, CH2Cl2/MeOH)
  6. dry with materialthe product was freeze-dried from MeCN/H2O

Sources & evidence

ORD record
ord-00128ce2209d431a869ea0fb4b251fcc
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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