Dimethylformamide → HCID 19103968, compound

HRID 1198118Notes

Reaction equation

HRID 1198118 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 178516071HCID 178516071, compound

Product 1

HCID 19103968HCID 19103968, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-hydroxypyridine (6.0 g), N-(4-bromobutyl)phthalimide (17.8 g), potassium carbonate (8.7 g) and N,N-dimethylformamide (DMF) (80 ml) was stirred at 100° C. for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off under reduced pressure. The oily residue was subjected to a silica gel column chromatography. From the fraction eluted with chloroform-ethyl acetate (4:1 v/v), N-[4-(2-pyridyloxy)butyl]phthalimide (4.4 g, 23%) was obtained Recrystallization of the product from ether gave colorless prisms, m.p. 77° C. to 78° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off under reduced pressure
  5. washFrom the fraction eluted with chloroform-ethyl acetate (4:1 v/v)

Sources & evidence

ORD record
ord-85bcc22e94fe4a97a984ce9d70cbd22a
Source dataset
uspto-grants-1994_01
Patent number
US05280022

Reaction notes

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