Ammonium Chloride → HCID 135737584, compound

HRID 1763501Notes

Reaction equation

HRID 1763501 reaction equation
[C:1]([C:4]1[CH:16]=[C:15]2[N:6]([C:7](=[O:17])[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=32)[N:5]=1)(=[O:3])[CH3:2].CC(C)=O.[C:22]1([Mg]Br)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OCC)C.[NH4+].[Cl-]>O1CCCC1>[OH:3][C:1]([C:4]1[CH:16]=[C:15]2[N:6]([C:7](=[O:17])[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=32)[N:5]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 135737581HCID 135737581, compoundHCID 178467673HCID 178467673, compound

Product 1

HCID 135737584HCID 135737584, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.0 g (0.022 mole) of the methyl ketone 2-acetylpyrazolo[1,5-c]quinazolin-5(6H)-one prepared as in Example 4A is suspended under argon in dry distilled tetrahydrofuran (100 ml) and treated quickly with 7.0 ml (~1.0 equivalent) of 3M C6H5MgBr/ethyl ether. The mixture is stirred for 5 minutes and another 15 ml (~2 equivalents) of the Grignard reagent is quickly added. The reaction mixture (dark brown) is stirred at room temperature for 30 minutes and then refluxed for another 30 minutes, cooled down to room temperature and the resulting reddish solution is treated with 8.0 ml of saturated NH4Cl solution. The mixture is diluted with 70 ml tetrahydrofuran and stirred at room temperature for ~1 hour. The inorganic salts are filtered off and washed well with tetrahydrofuran (30 ml) and CHCl3 (50 ml). The filtrates are combined and stripped to dryness. Yield: 8.4 g; 3 spots on TLC.

Workup

  1. customin dry
  2. distillationdistilled tetrahydrofuran (100 ml)
  3. stirringThe reaction mixture (dark brown) is stirred at room temperature for 30 minutes
  4. temperaturerefluxed for another 30 minutes
  5. stirringstirred at room temperature for ~1 hour
  6. filtrationThe inorganic salts are filtered off
  7. washwashed well with tetrahydrofuran (30 ml) and CHCl3 (50 ml)

Sources & evidence

ORD record
ord-878ac4b67de84caf80a1394b7542a9bb
Source dataset
uspto-grants-1978_09
Patent number
US04112096

Reaction notes

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