Ammonium Chloride → HCID 19102569, compound

HRID 1198543Notes

Reaction equation

HRID 1198543 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].[C:21]1([Mg]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>O1CCCC1>[C:21]1([CH:16]([OH:17])[C:15]2[CH:18]=[CH:19][CH:20]=[C:13](/[CH:12]=[CH:11]/[C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)[CH:14]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10801254HCID 10801254, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 19102569HCID 19102569, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[2(E)-(quinolin-2-yl)ethenyl] benzaldehyde (5.9 g, 22.8 mmol) in tetrahydrofuran (20 ml) was added to a stirred solution of phenyl magnesium bromide [prepared from bromobenzene (4.3 g, 27.4 mmol) and magnesium turnings(0.66 g, 27.4 mg atom) in tetrahydrofuran (50 ml) at ca 40° C.] at 10°-15° C. The dark solution was stirred for 1 hour at room temperature, poured onto saturated ammonium chloride solution and extracted with dichloromethane. The extract was dried and evaporated and the residue was crystallised from ethyl acetate.

Workup

  1. extractionextracted with dichloromethane
  2. customThe extract was dried
  3. customevaporated
  4. customthe residue was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-5d1bf32f8d664609b477409c5e5965ff
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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