Hydroxyamine hydrochloride → HCID 53675818, compound

HRID 977181Notes

Reaction equation

HRID 977181 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:19][CH2:20][C:21](=O)[CH3:22])=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.Cl.[NH2:25][OH:26]>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:19][CH2:20][C:21](=[N:25][OH:26])[CH3:22])=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochloride2×HCID 10806148HCID 10806148, compound

Product 1

HCID 53675818HCID 53675818, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

The product from Example 24 (0.50 g, 0.0015 mol), hydroxylamine hydrochloride (0.21 g, 0.0031 mol) and 4 Å molecular sieves were suspended in pyridine (10 ml) and heated at 60° C. for 14 h. A further amount of hydroxylamine hydrochloride (0.42 g, 0.0062 mol) was added and the reaction mixture heated under reflux for a further 24 h. The reaction mixture was diluted with ethyl acetate (30 ml) and filtered through hiflo. The mixture was washed with 1N hydrochloric acid (100 ml), the acid layer was back extracted with ethyl acetate (2×20 ml) and the combined organic layers were washed consecutively with water (20 ml), saturated sodium hydrogen carbonate solution (20 ml) and brine (20 ml), then dried (MgSO4), filtered, and concentrated in vacuo to give a white solid. This was recrystallised from ethanol/water to give a white crystalline solid; yield=278 mg. Mp=196°-198° C. Found: C, 62.93; H, 4.37; N, 8.10. C18H15ClN2O3 requires C, 63.07; H, 4.41; N, 8.17. δ (360 MHz, DMSO-d6), 1.60 (3H, s, CH3), 4.06 (2H, s, OCH2), 7.28 (1H, dd, J=8.6 and 2.1 Hz, 6-H), 7.32-7.48 (6H, m, aromatics), 7.78 (1H, d, J=8.7 Hz, 5-H), 10.88 (1H, s, NOH), 11.92 (1H, s, br, NH). MS (CI) m/z=343 [MH]+.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for a further 24 h
  3. filtrationfiltered through hiflo
  4. washThe mixture was washed with 1N hydrochloric acid (100 ml)
  5. extractionthe acid layer was back extracted with ethyl acetate (2×20 ml)
  6. washthe combined organic layers were washed consecutively with water (20 ml), saturated sodium hydrogen carbonate solution (20 ml) and brine (20 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a white solid
  11. customThis was recrystallised from ethanol/water
  12. customto give a white crystalline solid

Sources & evidence

ORD record
ord-75adc438f9eb438f867714987e3820a2
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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