Hydroxyamine hydrochloride → HCID 54400138, compound

HRID 330517Notes

Reaction equation

HRID 330517 reaction equation
C[O-].[Na+].[ClH:4].[NH2:5][OH:6].Cl[C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[C:13]2[CH2:18][C:19]#[N:20]>CO>[OH:6][N:5]=[C:19]([NH2:20])[CH2:18][C:13]1[C:14]2[C:9](=[C:8]([Cl:4])[CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 10942334Sodium Methoxide2×HCID 70357837HCID 70357837, compound

Product 1

HCID 54400138HCID 54400138, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of NaOMe (25 wt % in MeOH, 1.02 mL, 4.46 mmol), MeOH (4 mL), and hydroxylamine hydrochloride (310 mg, 4.46 mmol) was heated at reflux for 20 minutes. 5-Chloro-2-naphthalenylacetonitrile (600 mg, 2.98 mmol) and additional MeOH (4 mL) were added and heating was continued overnight. Additional hydroxylamine hydrochloride (150 mg, 2.16 mmol) and NaOMe (25 wt % in MeOH, 490 L, 2.14 mmol) were added and heating was resumed for 4 hours. The mixture was cooled, concentrated, and suspended in H2O. The solid was collected by filtration and triturated with ether to give a pale yellow solid (478 mg, 69%), m.p. 121°-125° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 minutes
  3. temperatureheating
  4. temperatureheating
  5. waitwas resumed for 4 hours
  6. temperatureThe mixture was cooled
  7. concentrationconcentrated
  8. filtrationThe solid was collected by filtration
  9. customtriturated with ether

Sources & evidence

ORD record
ord-7e6857df7e12407bac45134a88f0bc38
Source dataset
uspto-grants-1990_01
Patent number
US04897405

Reaction notes

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