Methanol → HCID 58081283, compound

HRID 928443Notes

Reaction equation

HRID 928443 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:18])=[N:8][C:9]2[C:14]([CH:15]=1)=[C:13]([CH3:16])[CH:12]=[C:11]([CH3:17])[CH:10]=2)=O)C.C1(C)C=CC=CC=1.CO.[K].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH3:18][C:7]1[C:6]([CH2:4][OH:3])=[CH:15][C:14]2[C:9](=[CH:10][C:11]([CH3:17])=[CH:12][C:13]=2[CH3:16])[N:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 17039663Ethyl 2,5,7-trimethylquinoline-3-carboxylateHCID 86636910HCID 86636910, compound

Product 1

HCID 58081283HCID 58081283, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2,5,7-trimethylquinoline-3-carboxylic acid ethyl ester (50 mg, 0.206 mmol) in DCM (1.7 ml) at −78° C. was added DIBAI-H 1M in Toluene (29.2 mg, 0.206 mmol). Reaction mixture was stirred 1 h at −78° C. Methanol (1 ml) was added to quench the reaction at −78° C. Mixture was then warmed up to 23° C. Sat. potassium/sodium tartrate solution (Rochelle's salt, 2 ml) was added and mixture was stirred 30 min at RT. Solid was filtered off and filtrate was extracted twice with DCM. Combined organic layer was washed with sat. NaHCO3 solution, brine, dried over sodium sulfate, filtered and evaporated to afford the title compound. HPLC (Method G) Rt=1.113 min, MS (Method V) [M+H]+=202.1

Workup

  1. customReaction mixture
  2. customto quench
  3. customthe reaction at −78° C
  4. temperatureMixture was then warmed up to 23° C
  5. stirringmixture was stirred 30 min at RT
  6. filtrationSolid was filtered off
  7. extractionfiltrate was extracted twice with DCM
  8. washCombined organic layer was washed with sat. NaHCO3 solution, brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-248cc8a96a504330bd71712345907167
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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