Hydrochloric Acid → HCID 86669828, compound

HRID 1620259Notes

Reaction equation

HRID 1620259 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[C:7]([CH2:18][CH3:19])=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([O:16][CH3:17])=[CH:11][CH:10]=2.ClC1C(C2OCCO2)=CC2C(=CC=C(OC)C=2)N=1.Cl>C1COCC1>[CH2:18]([C:7]1[C:6]([CH:2]=[O:1])=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:16][CH3:17])[CH:13]=2)[N:8]=1)[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 12191680HCID 12191680, compoundHCID 68182193HCID 68182193, compound

Product 1

HCID 86669828HCID 86669828, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[1,3]dioxolan-2-yl-2-ethyl-6-methoxyquinoline SMA 44002 (400 mg, 1.54 mmol) in THF (10 mL) in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added a 1 N aqueous HCl solution (5 mL) and the mixture was stirred overnight at RT, then for 1 h at 70° C. A 6 N aqueous HCl solution (2.5 mL) was then added and the mixture was stirred for 26 h at 70° C. THF was removed at 40° C. under vacuum before addition of a conc. NH4OH solution (5 mL). The solution was extracted with CH2Cl2 (50 mL) and the organic phase was isolated, washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum to give 2-ethyl-6-methoxyquinoline-3-carbaldehyde SMA 44004 as a brown oil (269 mg, 81% yield).

Workup

  1. waitfor 1 h at 70° C
  2. stirringthe mixture was stirred for 26 h at 70° C
  3. customTHF was removed at 40° C. under vacuum before addition of a conc. NH4OH solution (5 mL)
  4. extractionThe solution was extracted with CH2Cl2 (50 mL)
  5. customthe organic phase was isolated
  6. washwashed with brine (10 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated at 40° C. under vacuum

Sources & evidence

ORD record
ord-e5b154a37d1f4be2b0a3a936652fa268
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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