Ethylamine → HCID 86669834, compound

HRID 1620299Notes

Reaction equation

HRID 1620299 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:17])=[C:7]([O:14][CH2:15][CH3:16])[CH:8]=2)[N:3]=1.[CH2:18]([NH2:20])[CH3:19]>>[CH2:15]([O:14][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[F:17])[N:3]=[C:2]([NH:20][CH2:18][CH3:19])[C:11]([CH:12]=[O:13])=[CH:10]2)[CH3:16]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 86669835HCID 86669835, compound2×

Product 1

HCID 86669834HCID 86669834, compoundYield 56%

Conditions

Temperature
150 °C

Procedure

A solution of 2-chloro-6-ethoxy-7-fluoroquinoline-3-carbaldehyde SMA 44100 (110 mg, 0.43 mmol) in ethylamine (2.0 M in THF, 2.20 mL, 4.40 mmol) in a 10 mL microwave vial equipped with a magnetic stirrer was stirred for 3.5 h at 150° C. under microwave irradiation. After cooling to RT, the volatiles were removed at 40° C. under vacuum and the resulting yellow oil was taken up in a mixture of THF:1 N aq. HCl=50:50 (10 mL) and the mixture was stirred for 30 min at RT. THF was then removed at 40° C. under vacuum and the residue was basified with a 10 N aq. NaOH solution (pH=8) before extraction with CH2Cl2 (40 mL). The separated organic layer was washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 90:10) gave 6-ethoxy-2-(ethylamino)-7-fluoroquinoline-3-carbaldehyde SMA 44102 as a yellow solid (63 mg, 56% yield).

Workup

  1. temperatureAfter cooling to RT
  2. customthe volatiles were removed at 40° C. under vacuum
  3. additionthe resulting yellow oil was taken up in a mixture of THF
  4. stirring1 N aq. HCl=50:50 (10 mL) and the mixture was stirred for 30 min at RT
  5. customTHF was then removed at 40° C. under vacuum
  6. extractionthe residue was basified with a 10 N aq. NaOH solution (pH=8) before extraction with CH2Cl2 (40 mL)
  7. washThe separated organic layer was washed with brine (10 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated at 40° C. under vacuum
  11. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 90:10)

Sources & evidence

ORD record
ord-b0e604bc12a243d69cd5335756d52736
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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