Hydrochloric Acid → HCID 19100835, compound

HRID 1974901Notes

Reaction equation

HRID 1974901 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2C(=O)C3=CC=CC=C3C2=O)C=CC=1.[ClH:19].[CH3:20][O:21][NH2:22].C(=O)([O-])[O-].[Na+].[Na+].O.NN.Cl>C(O)C.O>[ClH:19].[ClH:19].[NH2:8][CH2:4][CH2:3][CH2:2][NH:22][O:21][CH3:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 521874O-Methylhydroxylamine hydrochlorideHCID 45355142-(3-Bromophenyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 19100835HCID 19100835, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

10 g (0.037 mol) of N-(3-bromophenyl)-phthalimide, 6.2 g (0.075 mol) of methoxyamine hydrochloride and 15.0 g of sodium carbonate are suspended in 150 ml of ethanol and refluxed for 12 hours. After cooling, the salts are separated off by filtration and the solvent is removed. The oil which remains is treated with ethyl acetate, the insoluble residue is separated off and the solvent is removed. The oil which remains is taken up in 25 ml of ethanol and 1.15 g (0.023 mol) of hydrazine hydrate is added. The solution is stirred for 30 minutes at 80° C. After the addition of 3 ml of concentrated hydrochloric acid the mixture is stirred for a further 30 minutes at 80° C. 10 ml of water is then added and the whole filtered. Concentration and recrystallization from ethanol give the desired product as colorless crystals.

Workup

  1. temperaturerefluxed for 12 hours
  2. temperatureAfter cooling
  3. customthe salts are separated off by filtration
  4. customthe solvent is removed
  5. additionThe oil which remains is treated with ethyl acetate
  6. customthe insoluble residue is separated off
  7. customthe solvent is removed
  8. stirringis stirred for a further 30 minutes at 80° C
  9. concentrationConcentration and recrystallization from ethanol

Sources & evidence

ORD record
ord-be4584263a8e4087af0a9d5a73c2fa39
Source dataset
uspto-grants-1994_02
Patent number
US05284851

Reaction notes

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