4-Chlorobutyrophenone → HCID 21505615, compound

HRID 1658808Notes

Reaction equation

HRID 1658808 reaction equation
Cl([O-])(=O)(=O)=O.[C:6]([CH2:14][CH2:15][CH2:16][N+:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:27][N:26]=[C:25]([CH3:28])[CH:24]=2)=[CH:19][CH:18]=1)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.ClCCCC(C1C=CC=CC=1)=O.CC1C=C(C2C=CN=CC=2)ON=1.[BH4-].[Na+]>CO>[CH3:28][C:25]1[CH:24]=[C:23]([C:20]2[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][CH2:14][CH:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[OH:13])[CH2:18][CH:19]=2)[O:27][N:26]=1

Participants

6

Reactant 4

HCID 2535334-ChlorobutyrophenoneHCID 4311764Sodium borohydrideHCID 11126553HCID 11126553, compoundHCID 21505627HCID 21505627, compound

Product 1

HCID 21505615HCID 21505615, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 4.1 g. portion of 1-(3-benzoylpropyl)-4-(3-methyl-5-isoxazolyl)pyridinium perchlorate [prepared by the reaction of γ-chlorobutyrophenone and 4-(3-methyl-5-isoxazolyl)pyridine as described in the previous examples] in 200 ml. of methanol is added, portionwise with stirring, 4.1 g. of sodium borohydride. The mixture is allowed to stand at room temperature overnight, evaporated to about 1/2 volume and poured into ice water. The white solid is collected and recrystallized from acetonitrile, m.p. 108°-109°C.

Workup

  1. customevaporated to about 1/2 volume
  2. additionpoured into ice water
  3. customThe white solid is collected
  4. customrecrystallized from acetonitrile, m.p. 108°-109°C.

Sources & evidence

ORD record
ord-ad0bec61da7a4b9b9562ca743663b6f0
Source dataset
uspto-grants-1976_06
Patent number
US03966748

Reaction notes

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