Guaiacol → HCID 22054602, compound

HRID 1006142Notes

Reaction equation

HRID 1006142 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.Cl[C:16]1[C:25]2[C:20](=[CH:21][C:22]([CH2:26][OH:27])=[CH:23][CH:24]=2)[N:19]=[C:18]([CH3:28])[CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:48][O:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=1O.[NH:57]1[CH2:61][CH2:60][CH2:59][CH2:58]1.[C:62]([OH:67])(=[O:66])[C:63]([OH:65])=[O:64]>ClCCl.C(O)C>[C:62]([OH:67])(=[O:66])[C:63]([OH:65])=[O:64].[CH3:48][O:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=1[O:27][CH2:26][C:22]1[CH:21]=[C:20]2[C:25]([C:16]([N:57]3[CH2:61][CH2:60][CH2:59][CH2:58]3)=[CH:17][C:18]([CH3:28])=[N:19]2)=[CH:24][CH:23]=1

Participants

9

Reactant 6

HCID 460GuaiacolHCID 971Oxalic AcidHCID 11776TriphenylphosphineHCID 31268PyrrolidineHCID 5363146Diisopropyl azodicarboxylateHCID 11264243HCID 11264243, compound

Product 1

HCID 22054602HCID 22054602, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Diisopropylazodicarboxylate (97 mg, 0.48 mmol) was added dropwise at r.t. to a solution of (4-chloro-2-methyl-quinolin-7-yl)-methanol (example 2c, 100 mg, 0.48 mmol), triphenylphosphine (126 mg, 0.48 mmol), 2-methoxyphenol (60 mg, 0.48 mmol) in dichloromethane (2.5 mL). After shaking 24 h at r.t., the solvent was evaporated, and the residue was taken up in pyrrolidine (1.37 g, 19.2 mmol) and shaken for 23 h at 80° C. After cooling the reaction mixture was partitioned between sat. aq. ammonium chloride solution and dichloromethane, the organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, dichloromethane/methanol 19:1) yielded a yellowish solid which was dissolved in ethanol and treated with 20% ethanolic oxalic acid solution. The precipitate was collected by filtration and dried to afford the title compound (90 mg, 43%). Off-white solid, ISP-MS: m/e=349.4 ([M+H—C2H2O4]+).

Workup

  1. customthe solvent was evaporated
  2. stirringshaken for 23 h at 80° C
  3. temperatureAfter cooling the reaction mixture
  4. customwas partitioned between sat. aq. ammonium chloride solution and dichloromethane
  5. washthe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customChromatography (SiO2, dichloromethane/methanol 19:1) yielded a yellowish solid which
  9. filtrationThe precipitate was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-3460d1419998418fbea719f32b1273b2
Source dataset
uspto-grants-2004_09
Patent number
US06787558B2

Reaction notes

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