Hydrochloric Acid → HCID 86669832, compound

HRID 1620277Notes

Reaction equation

HRID 1620277 reaction equation
[CH2:1]([C:5]1[C:14]([CH:15]2OCC[O:16]2)=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:20][CH3:21])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].Cl>C1COCC1>[CH2:1]([C:5]1[C:14]([CH:15]=[O:16])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:20][CH3:21])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68182246HCID 68182246, compound2×

Product 1

HCID 86669832HCID 86669832, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-butyl-3-(1,3-dioxolan-2-yl)-6-methoxyquinoline SMA 44042 (847 mg, 2.95 mmol) in THF (20 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added a 12 N aqueous HCl solution (5.0 mL, 60.0 mmol) and the mixture was stirred overnight at RT then for 3 h at 70° C. After cooling to RT, THF was removed at 40° C. under vacuum before addition of a 10 N aqueous NaOH solution until neutral pH. The residue was then taken up in CH2Cl2 (50 mL) and the organic layer was isolated, washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent CH2Cl2:EtOAc=100:0 to 98:2) gave 2-butyl-6-methoxyquinoline-3-carbaldehyde SMA 44044 as an orange solid (583 mg, 81% yield).

Workup

  1. waitfor 3 h at 70° C
  2. temperatureAfter cooling to RT
  3. customTHF was removed at 40° C. under vacuum before addition of a 10 N aqueous NaOH solution until neutral pH
  4. customthe organic layer was isolated
  5. washwashed with brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated at 40° C. under vacuum
  9. customPurification by column chromatography (SiO2, eluent CH2Cl2:EtOAc=100:0 to 98:2)

Sources & evidence

ORD record
ord-772385656fb54f8fa4941c6c2bf50974
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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