Ammonium Chloride → HCID 13882400, compound

HRID 745220Notes

Reaction equation

HRID 745220 reaction equation
[Mg].[CH3:2][C:3]1[N:8]=[C:7]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=1.[CH3:18][CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)=[O:21].[Cl-].[NH4+]>O1CCCC1>[CH3:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:20]([C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)([OH:21])[CH2:19][CH3:18])=[CH:13][CH:12]=2)[N:8]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 680044-FluoropropiophenoneHCID 5462224MagnesiumHCID 13882399HCID 13882399, compound

Product 1

HCID 13882400HCID 13882400, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a Gringard reactant prepared from 2.2 g. of magnesium turnings and 25 g. of 4-[(6-methylpyrid-2-yl)-methoxy]-bromobenzene in 120 ml. of dry tetrahydrofurane a solution of 9.1 g. of 4-fluoropropiophenone in 45 ml. of tetrahydrofurane is added dropwise at 0° C. The reaction mixture is stirred at room temperature for two additional hours, and is then decomposed with a saturated aqueous ammonium chloride solution, under cooling. The aqueous phase is extracted with tetrahydrofurane. The tetrahydrofurane phase is washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and evaporated in vacuo. Crystallization of the crude product from a mixture of ethyl acetate and n-hexane yields 15.2 g. of the title compound, melting at 103° to 104° C.

Workup

  1. customTo a Gringard reactant prepared from 2.2 g
  2. temperatureunder cooling
  3. extractionThe aqueous phase is extracted with tetrahydrofurane
  4. washThe tetrahydrofurane phase is washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customCrystallization of the crude product
  8. additionfrom a mixture of ethyl acetate and n-hexane
  9. customyields 15.2 g

Sources & evidence

ORD record
ord-3f8e17c308cf47f99bf9d0265c294e51
Source dataset
uspto-grants-1986_07
Patent number
US04598080

Reaction notes

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