o-Vanillin → HCID 136055533, compound

HRID 1367642Notes

Reaction equation

HRID 1367642 reaction equation
[CH3:1][C:2]1[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4](=[O:12])[C:5]2[CH:11]=[N:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:19][O:20][C:21]1[C:26]([OH:27])=[C:25]([CH:28]=O)[CH:24]=[CH:23][CH:22]=1>C(O)(=O)C>[OH:27][C:26]1[C:21]([O:20][CH3:19])=[CH:22][CH:23]=[CH:24][C:25]=1/[CH:28]=[CH:1]/[C:2]1[N:3]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:4](=[O:12])[C:5]2[CH:11]=[N:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 8991o-VanillinHCID 58938502HCID 58938502, compound

Product 1

HCID 136055533HCID 136055533, compoundYield 9.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The crude compound 18 (0.436 mg, 1.84 mmol) was mixed with o-vaniline (0.60 g, 4.0 mmol) in 5 mL of glacial acetic acid. The reaction mixture was heated in a microwave for 2 h keeping temperature constant at 150° C. The reaction mixture was concentrated in vacuo, co-evaporated several times with toluene and purified by flash chromatography (CH2Cl2/EtOAc) to give 65 mg of the target compound 19 (8% yield for two last steps). MS: m/z+372.2 [M+H]+.

Workup

  1. temperatureThe reaction mixture was heated in a microwave for 2 h
  2. customconstant at 150° C
  3. concentrationThe reaction mixture was concentrated in vacuo, co-evaporated several times with toluene
  4. custompurified by flash chromatography (CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-7fa9d830c7e04542ab054b5a3af533c2
Source dataset
uspto-grants-2011_02
Patent number
US07893260B2

Reaction notes

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