Ammonium Chloride → HCID 86761357, compound

HRID 1011432Notes

Reaction equation

HRID 1011432 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][CH:6]=2.[CH:14]([Mg]Cl)([CH3:16])[CH3:15].[CH:19]1(C)CC[CH:22](C(C)C)[CH:21]([S:28]([O-])=[O:29])[CH2:20]1.[NH4+].[Cl-]>C1COCC1>[CH3:15][C:14]1[CH:16]=[CH:22][C:21]([S:28]([C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][CH:6]=3)=[O:29])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 231597643-Bromo-5-methoxyquinolineHCID 66813815HCID 66813815, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 86761357HCID 86761357, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution 3-bromo-5-methoxyquinoline (2.37, 10 mmol) prepared in stage B in dried THF (35 mL) is added a solution of isopropylmagnesium chloride (16.6 mL, 30 mmol) at −78° C. The solution is stirred at −78° C. under nitrogen atmosphere for 3 hours. Menthyl sulfinate (8.8 g, 30 mmol) is added and the resulting solution is stirred for a further 24 hours. The reaction mixture is then hydrolysed with saturated aqueous NH4Cl solution. After extraction of the aqueous phase, the combined organic layers are dried (MgSO4), evaporated giving the title compound.

Workup

  1. stirringthe resulting solution is stirred for a further 24 hours
  2. extractionAfter extraction of the aqueous phase
  3. dry with materialthe combined organic layers are dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-7e24c7eea64c44bf94d44785c0ff3d2d
Source dataset
uspto-grants-2011_07
Patent number
US07977354B2

Reaction notes

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