Hydrazine hydrate (1:1) → HCID 59829898, compound

HRID 1947181Notes

Reaction equation

HRID 1947181 reaction equation
COC[O:4][C:5](=O)[C:6]1[CH:11]=[C:10]([Br:12])[C:9]([O:13][CH2:14][O:15][CH3:16])=[CH:8][C:7]=1[O:17][CH2:18][O:19][CH3:20].O.[NH2:23][NH2:24]>C(O)C>[Br:12][C:10]1[C:9]([O:13][CH2:14][O:15][CH3:16])=[CH:8][C:7]([O:17][CH2:18][O:19][CH3:20])=[C:6]([CH:11]=1)[C:5]([NH:23][NH2:24])=[O:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59829894HCID 59829894, compound

Product 1

HCID 59829898HCID 59829898, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

5-bromo-2,4-bis-methoxymethoxybenzoic acid methoxymethylester (IM3-d: 4.36 g, 11.9 mmol), ethanol (15 mL) and hydrazine monohydrate (0.96 mL, 29.8 mmol) were placed in a 100 mL eggplant shaped flask and stirred at 70° C. for 27 hours. After completing the reaction, the reaction mixture was extracted with methylene chloride, and the organic layer was washed with saturated sodium chloride solution and then concentrated under reduced pressure. The solid material thus obtained was suspended in hexane for purification to obtain the title compound (IM4-d: 1.8 g, 46%).

Workup

  1. customthe reaction
  2. extractionthe reaction mixture was extracted with methylene chloride
  3. washthe organic layer was washed with saturated sodium chloride solution
  4. concentrationconcentrated under reduced pressure
  5. customThe solid material thus obtained
  6. customwas suspended in hexane for purification

Sources & evidence

ORD record
ord-16589bc198e443fea3fe8cfd291ea4d4
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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