Sodium Hydroxide → HCID 178438308, compound

HRID 247601Notes

Reaction equation

HRID 247601 reaction equation
Cl.[NH2:2][OH:3].[CH2:4]([C:7]12[CH2:13][CH:10]([CH:11]=[CH:12]1)[CH:9]1[C:14]([O:16][C:17](=[O:18])[CH:8]21)=[O:15])[CH:5]=[CH2:6].[OH-].[Na+]>O>[OH:3][N:2]=[C:17]([CH:8]1[CH:9]([C:14]([OH:16])=[O:15])[CH:10]2[CH2:13][C:7]1([CH2:4][CH:5]=[CH2:6])[CH:12]=[CH:11]2)[OH:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 54206110Allylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride

Product 1

HCID 178438308HCID 178438308, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

139 g (2 mol) of hydroxylamine hydrochloride are dissolved in 200 ml of water, 408 g (2 mol) of allylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride (prepared according to Example 1 of U.S. Pat. No. 3,105,839) are added to the solution and, with vigorous stirring, 160 g of 50% aqueous NaOH solution are then added dropwise. The mixture is subsequently heated for 1 hour under reflux, the water and traces of oily components are distilled off and the residue is taken up in toluene. The toluene phase is filtered in order to remove the sodium chloride, and the toluene is subsequently removed by rotary evaporation at 150° C. and 2000 Pa, affording 402.6 g of the product (91.5% of theory) as a pale brown viscous liquid with a viscosity of 1.28 Pa.s at 80° C.

Workup

  1. additionare then added dropwise
  2. temperatureThe mixture is subsequently heated for 1 hour
  3. temperatureunder reflux
  4. distillationthe water and traces of oily components are distilled off
  5. filtrationThe toluene phase is filtered in order
  6. customto remove the sodium chloride
  7. customthe toluene is subsequently removed by rotary evaporation at 150° C.

Sources & evidence

ORD record
ord-6d0b20a419104fe39f36494691a4d953
Source dataset
uspto-grants-1987_11
Patent number
US04709047

Reaction notes

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