HCID 44138603, compound → HCID 68182225, compound

HRID 1620219Notes

Reaction equation

HRID 1620219 reaction equation
[CH2:1]([NH:8][C:9]1[C:18]([CH:19]=[O:20])=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:21][CH3:22])[CH:15]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH2:1]([NH:8][C:9]1[C:18]([CH2:19][OH:20])=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:21][CH3:22])[CH:15]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 44138603HCID 44138603, compound2×

Product 1

HCID 68182225HCID 68182225, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(benzylamino)-6-methoxyquinoline-3-carbaldehyde SLA 41002 (0.40 g, 1.37 mmol) in THF (50 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added sodium borohydride NaBH4 (0.24 g, 6.35 mmol) and the mixture was stirred overnight at RT then cooled in an ice bath before quenching by addition of a 1 N aq. HCl solution (15 mL). After stirring for 15 min at that temperature, the mixture was basified to pH=9 with a 2 N aq. NaOH solution. THF was then removed at 40° C. under vacuum and the solution was extracted with CH2Cl2 (200 mL), washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated under vacuum to give (2-(benzylamino)-6-methoxyquinolin-3-yl)methanol SLA 41006 as a yellow solid (0.395 g, 98% yield).

Workup

  1. temperaturethen cooled in an ice bath
  2. custombefore quenching by addition of a 1 N aq. HCl solution (15 mL)
  3. stirringAfter stirring for 15 min at that temperature
  4. customTHF was then removed at 40° C. under vacuum
  5. extractionthe solution was extracted with CH2Cl2 (200 mL)
  6. washwashed with brine (20 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9f67c1bb3df44d528bfc7d59897aec8e
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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