Nitrogen → HCID 10106224, compound

HRID 2371567Notes

Reaction equation

HRID 2371567 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:11]([O:18][CH3:19])(=[O:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14].[H-].[Na+].N#N>O>[CH3:16][O:15][C:13](=[O:14])[CH:12]([C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[C:11]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 947NitrogenHCID 69402-Bromobenzoic acidHCID 7943Dimethyl malonateHCID 24758Sodium hydride2×

Product 1

HCID 10106224HCID 10106224, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a rapidly stirred cold suspension (0° C.) of 2-bromobenzoic acid (30.0 g, 149.32 mmol), cuprous bromide (2.14 g, 14.93 mmol) and dimethyl malonate (300 mL) was added NaH (80% in mineral oil, 10.75 g, 358.37 mmol) over a 30 minute period, while a stream of dry N2 was passed over the mixture. After the addition of the NaH had been completed, the mixture was stirred for 10 minutes at room temperature and 30 minutes at 70° C. (external oil bath temperature). At this point, the suspension had turned to a solid mass, which was dissolved in H2O (1000 mL). The aqueous layer was extracted with diethyl ether (3×500 mL) and was acidified with HCl (2N). The mixture was extracted with EtOAc and dried over MgSO4. Evaporation gave an off-white solid which was recrystallized from Et2O/hexane (-20° C.) to give a white solid (34.2 g, 90.9%).

Workup

  1. extractionThe aqueous layer was extracted with diethyl ether (3×500 mL)
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. customEvaporation
  5. customgave an off-white solid which
  6. customwas recrystallized from Et2O/hexane (-20° C.)

Sources & evidence

ORD record
ord-c9c287a397554876b55356790e4f2d72
Source dataset
uspto-grants-1992_03
Patent number
US05093496

Reaction notes

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