HCID 14780584, compound → HCID 14780585, compound

HRID 1650139Notes

Reaction equation

HRID 1650139 reaction equation
C[O:2][C:3](=O)/[CH:4]=[CH:5]/[C:6]1[C:7]([N:23]([CH3:25])[CH3:24])=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[CH3:25][N:23]([CH3:24])[C:7]1[C:6](/[CH:5]=[CH:4]/[CH2:3][OH:2])=[C:15]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1

Participants

4

Reactant 2

HCID 14780584HCID 14780584, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14780585HCID 14780585, compoundYield 108.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(E)-Methyl-3-[2-(dimethylamino)-4-(4-fluorophenyl)-3-quinolinyl]-2-propenoate (4.60 g) is dissolved in 40 ml of dichloromethane at -78° C. under an atmosphere of nitrogen. A 1 M solution of diisobutylaluminum hydride (DIBAL) (29 ml, 2.2 equivalents), in dichloromethane is added dropwise, the reaction stirred for one hour, and quenched by adding 15 ml of an aqueous saturated solution of sodium sulfate and removing the cooling bath. The reaction mixture is filtered through Celite and the filtrate dried (magnesium sulfate) and evaporated to give 4.61 g of (E)-3-[2-(dimethylamino)-4-(4-fluorophenyl)-3-quinolinyl]-2-propen-1-ol as an orange oil; 1H NMR (chloroform-d): δ 7.72 (d, 1H), 7.50-7.30 (m, 1H), 7.20-6.98 (m, 6H), 6.31 (d, 1H), 5.72 (dt, 1H), 3.99 (bd, 2H), 2.96 (s, 6H), 1.54 (bs, 1H) ppm.

Workup

  1. customquenched
  2. additionby adding 15 ml of an aqueous saturated solution of sodium sulfate
  3. customremoving the cooling bath
  4. filtrationThe reaction mixture is filtered through Celite
  5. dry with materialthe filtrate dried (magnesium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-5eac852b956748b1a935242babf33d49
Source dataset
uspto-grants-1990_05
Patent number
US04923861

Reaction notes

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