Hydrochloric Acid → HCID 13247647, compound

HRID 543318Notes

Reaction equation

HRID 543318 reaction equation
[Mg].ClC1C=CC(Br)=CC=1.C(C1C(N2C=CN=C2)=NC=CC=1)#N.[Cl-].[NH4+].[Cl:25][C:26]1[CH:44]=[CH:43][C:29]([C:30]([C:32]2[C:33]([N:38]3[CH:42]=[CH:41][N:40]=[CH:39]3)=[N:34][CH:35]=[CH:36][CH:37]=2)=N)=[CH:28][CH:27]=1.Cl.CC[O:48]CC>C1C=CC=CC=1>[Cl:25][C:26]1[CH:44]=[CH:43][C:29]([C:30]([C:32]2[C:33]([N:38]3[CH:42]=[CH:41][N:40]=[CH:39]3)=[N:34][CH:35]=[CH:36][CH:37]=2)=[O:48])=[CH:28][CH:27]=1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 7806p-BromochlorobenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 132476462-(1H-Imidazol-1-yl)pyridine-3-carbonitrileHCID 20206220HCID 20206220, compound

Product 1

HCID 13247647HCID 13247647, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A Grignard reagent which is prepared by reacting 1.9 g of magnesium with 15 g of p-chlorobromobenzene in 150 ml of anhydrous ether is added to a suspension of 10.2 g of 3-cyano-2-(1-imidazolyl)pyridine in 200 ml of benzene at 30°-35° C. After the addition is complete, the whole mixture is stirred at room temperature for 1.5 hours. The reaction mixture is treated with an aqueous ammonium chloride solution under ice cooling. To the benzene layer containing the resulting 3-(4-chlorobenzimidoyl)-2-(1-imidazolyl)pyridine is added dilute hydrochloric acid and the mixture is stirred at 35° C. for 10 minutes for hydrolysis. The dilute hydrochloric acid layer is separated and made alkaline with sodium hydroxide and then extracted with chloroform. The chloroform layer is washed with water, dried and concentrated to give 3-(4-chlorobenzoyl)-2-(1-imidazolyl)pyridine as an oil in high yield. This oily product can be used in the next reaction without isolation, but when the oil is treated with toluene, crystallization takes place. Upon recrystallization from toluene the product is obtained as white crystals, melting at 118°-120° C.

Workup

  1. additionAfter the addition
  2. stirringthe mixture is stirred at 35° C. for 10 minutes for hydrolysis
  3. customThe dilute hydrochloric acid layer is separated
  4. extractionextracted with chloroform
  5. washThe chloroform layer is washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ee96b161857848ae95f255b3e8ca2a4b
Source dataset
uspto-grants-1987_04
Patent number
US04661603

Reaction notes

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