Dimethylformamide → HCID 15296705, compound

HRID 1647860Notes

Reaction equation

HRID 1647860 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:17]([OH:19])=O)=[C:10]2[O:13][CH:14]([CH3:16])[CH3:15])=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[CH:31]([NH2:34])([CH3:33])[CH3:32]>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:17]([NH:34][CH:31]([CH3:33])[CH3:32])=[O:19])=[C:10]2[O:13][CH:14]([CH3:15])[CH3:16])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6363IsopropylamineHCID 65578Oxalyl chlorideHCID 14256756HCID 14256756, compound

Product 1

HCID 15296705HCID 15296705, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a room temperature solution of 7-methoxy-1-(1-methylethoxy)-2-naphthalenecarboxylic acid (200 0.77 mmol) in 5 mL of THF is added oxalyl chloride (0.08 mL, 0.92 mmol) followed by DMF (0.015 mL). The solution is stirred at room temperature for 2 hours. Isopropylamine (0.39 mL) is added and the reaction mixture is stirred at room temperature overnight. The reaction mixture is diluted with ethyl acetate and washed with 1N HCI, saturated NaHCO3, and brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. The crude product is chromatographed on silica gel eluting with hexane:ethyl acetate (2:1) to provide 7-methoxy-1-(1-methylethoxy)-N-(1-methylethyl)-2-naphthalenecarboxamide in 72% yield; mp 62°-64° C.

Workup

  1. stirringthe reaction mixture is stirred at room temperature overnight
  2. washwashed with 1N HCI, saturated NaHCO3, and brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product is chromatographed on silica gel eluting with hexane:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-2d005df3a78848fb9577d12fdabeb4b3
Source dataset
uspto-grants-1995_07
Patent number
US05434188

Reaction notes

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