Sodium Bicarbonate → HCID 136140210, compound

HRID 2309140Notes

Reaction equation

HRID 2309140 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:13]2[CH2:18][C:17](=[O:19])[C:16]([C:20](=O)[CH2:21][CH2:22][CH3:23])=[C:15]([OH:25])[CH2:14]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(=[O:3])[CH3:2].Cl.[CH2:27]([O:30][NH2:31])[CH:28]=[CH2:29].C(=O)(O)[O-].[Na+]>CO>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:13]2[CH2:18][C:17](=[O:19])[C:16]([C:20](=[N:31][O:30][CH2:27][CH:28]=[CH2:29])[CH2:21][CH2:22][CH3:23])=[C:15]([OH:25])[CH2:14]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 178450330HCID 178450330, compound

Product 1

HCID 136140210HCID 136140210, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3 g of 5-(3-acetylamino-4-methoxyphenyl)-2-butyryl-3-hydroxycyclohex-2-en-1-one were stirred together with 0.95 g of O-allylhydroxylamine hydrochloride and 0.8 g of sodium bicarbonate in 40 ml of methanol for 16 hours. The mixture was evaporated down, mixed with methylene chloride, washed thoroughly with water, dried and evaporated down again. The residue which remained was stirred with diisopropyl ether and the product was filtered off under suction. 2.0 g (57% yield) of 5-(3-acetylamino-4-methoxyphenyl)-2-(1-allyloxyiminobutyl)-3-hydroxycyclohex-2-en-1-one of melting point 136°-137° C. were obtained (compound No. 11).

Workup

  1. customThe mixture was evaporated down
  2. additionmixed with methylene chloride
  3. washwashed thoroughly with water
  4. customdried
  5. customevaporated down again
  6. filtrationthe product was filtered off under suction

Sources & evidence

ORD record
ord-8764db1ec07b49b994b2a0b26986c1ef
Source dataset
uspto-grants-1987_09
Patent number
US04692553

Reaction notes

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