Hydroxyamine hydrochloride → HCID 135980741, compound

HRID 965411Notes

Reaction equation

HRID 965411 reaction equation
[C:1]([C:3](=[N:7][O:8][CH3:9])[C:4](N)=[O:5])#[N:2].C(=O)(O)[O-:11].[Na+].Cl.[NH2:16][OH:17]>O>[C:4]([C:3](=[N:7][O:8][CH3:9])[C:1](=[N:16][OH:17])[NH2:2])([OH:11])=[O:5]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 534247972-Cyano-2-(methoxyimino)acetamide

Product 1

HCID 135980741HCID 135980741, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a suspension of 2-cyano-2-methoxyimino-acetamide (24.4 g, 0.19 mol) and sodium bicarbonate (32.2 g, 0.38 mol) in water, hydroxylamine hydrochloride (13.3 g, 0.19 mol) in water (18.4 g) was added dropwise at 80° to 85° C. The mixture was stirred at the same temperature for 3 hrs. Then, the reaction solution was concentrated followed by adjusting to pH 2.0 with concentrated hydrochloric acid and then cooling to separate crystals. The crystals were filtered off, washed with methanol (20 g) and dried to give 2-carboxy-2-methoxyimino-acetamidoxime (27.1 g). The crystal contained 14.8% of sodium chloride. Practical yield: 27.1×0.852=23.1 g. Yield: 74.8%.

Workup

  1. additionwas added dropwise at 80° to 85° C
  2. concentrationThen, the reaction solution was concentrated
  3. temperaturecooling
  4. customto separate crystals
  5. filtrationThe crystals were filtered off
  6. washwashed with methanol (20 g)
  7. customdried

Sources & evidence

ORD record
ord-791ea7c176f44afc951865db679f5e53
Source dataset
uspto-grants-1998_06
Patent number
US05773624

Reaction notes

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