Aluminium lithium hydride → HCID 59756873, compound

HRID 2196591Notes

Reaction equation

HRID 2196591 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][CH:13]=[C:12]2[C:21](OC)=[O:22]>O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][CH:13]=[C:12]2[CH2:21][OH:22]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59756874HCID 59756874, compound

Product 1

HCID 59756873HCID 59756873, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Lithium aluminum hydride (262 mg, 6.90 mmol) was suspended in tetrahydrofuran (20 mL) then cooled to −78° C. A solution of methyl 6,7-dimethoxyquinoline-4-carboxylate (1.55 g, 6.27 mmol) in tetrahydrofuran (20 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 4 hours. The reaction was quenched with ethyl acetate (6 mL) then added sodium sulfate decahydrate and warmed the mixture to room temperature, stirring overnight. The mixture was filtered and the filtrate was concentrated under vacuum. The remaining solid was triturated with dichloromethane, filtered and dried under high vacuum to give 1.2 g of (6,7-dimethoxyquinoline-4-yl)methanol as a light yellow solid. MS (ESI, pos. ion) m/z: 220.0 (M+1).

Workup

  1. customThe reaction was quenched with ethyl acetate (6 mL)
  2. temperatureadded sodium sulfate decahydrate and warmed the mixture to room temperature
  3. stirringstirring overnight
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe remaining solid was triturated with dichloromethane
  7. filtrationfiltered
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-edf78e5f10d8473f9190641248a01500
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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