Hydroxyamine hydrochloride → HCID 131714981, compound

HRID 1732066Notes

Reaction equation

HRID 1732066 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH2:12][CH2:13][CH2:14][C:15](=O)[C:7]1=[C:6]2[CH3:17].Cl.[NH2:19][OH:20]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH2:12][CH2:13][CH2:14][C:15](=[N:19][OH:20])[C:7]1=[C:6]2[CH3:17]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 13749125HCID 13749125, compound

Product 1

HCID 131714981HCID 131714981, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6,7,8,9-Tetrahydro-2-methoxy-10-methylpyrido[1,2-a]indol-9-one, (9.16 g, 0.04 mol, described in Example 15, Step 2), was dissolved in pyridine (180 mL). Hydroxylamine hydrochloride (5.56 g, 0.08 mol) was added and the resulting solution refluxed for 90 minutes. The reaction mixture was concentrated in vacuo to ~15 mL, water (200 mL) was added and the product was extracted with ether (2×50 mL). The combined organic extracts were washed with water (100 mL), 5% hydrochloric acid (50 mL), 10% aqueous sodium bicarbonate (100 mL), then dried over MgSO4, filtered, and evaporated to afford the desired oxime 9.2 g (94%) m.p. 174°-6° C.

Workup

  1. temperaturethe resulting solution refluxed for 90 minutes
  2. concentrationThe reaction mixture was concentrated in vacuo to ~15 mL, water (200 mL)
  3. additionwas added
  4. extractionthe product was extracted with ether (2×50 mL)
  5. washThe combined organic extracts were washed with water (100 mL), 5% hydrochloric acid (50 mL), 10% aqueous sodium bicarbonate (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-574971e378cc4eb7a46f20e03647c0cd
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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