Dimethylformamide → HCID 68590809, compound

HRID 1047946Notes

Reaction equation

HRID 1047946 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:15])[CH:12]=2)[CH2:7][N:6]1[C:16](=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=1[OH:24])=[O:4].CN(C=O)C.C([O-])([O-])=O.[K+].[K+].Br[CH2:38][CH2:39][CH3:40]>CCOC(C)=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:15])[CH:12]=2)[CH2:7][N:6]1[C:16](=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=1[O:24][CH2:38][CH2:39][CH3:40])=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 68590315HCID 68590315, compound

Product 1

HCID 68590809HCID 68590809, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
79 °C

Procedure

A 100 mL round bottom flask which contains 6-bromo-(2-hydroxoxy-3-methyl-benzoylamino)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid methyl ester (373, 0.39 g, 0.932 mmol) and a stirring bar is charged with dry DMF (10 mL). Stirring is initiated. K2SO4 (0.258 g, 1.86 mmol), KI (1 mg, 6 μM), and 1-bromopropane (0.2 mL, 2.24 mmol) are added in turn. The reaction flask is immersed in an oil bath and fitted with a reflux condenser. The oil bath is heated to 79° C. The reaction is stirred for 2 h at this temperature then the oil bath is turned off. After 16 h at ambient temperature, heating is reinitiated at 53° C. for an additional hour. Analysis by ttlc (silica, 1:1 EtOAc:Heptanes), indicates consumption of starting material and appearance of a spot with a slightly lower Rf. The reaction is again allowed to cool to ambient temperature and filtered through a bed of Celite. The resulting solution is diluted with EtOAc (60 mL) and washed repeatedly with brine (4×40 mL), and then dried over MgSO4, filtered and evaporated by pumping to a constant weight yields light yellow oil (0.42 g, 98%).

Workup

  1. customA 100 mL round bottom flask which contains
  2. customThe reaction flask is immersed in an oil bath
  3. customfitted with a reflux condenser
  4. stirringThe reaction is stirred for 2 h at this temperature
  5. temperatureheating
  6. waitis reinitiated at 53° C. for an additional hour
  7. customconsumption of starting material and appearance of a spot with a slightly lower Rf
  8. temperatureto cool to ambient temperature
  9. filtrationfiltered through a bed of Celite
  10. additionThe resulting solution is diluted with EtOAc (60 mL)
  11. washwashed repeatedly with brine (4×40 mL)
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. customevaporated

Sources & evidence

ORD record
ord-b82009afcff64428a4efcfb5cfd9dbbc
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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