Hydrochloric Acid → HCID 12852675, compound

HRID 1156824Notes

Reaction equation

HRID 1156824 reaction equation
[C:1]([C:4]1[C:8](=[O:9])[NH:7][C:6]2=[CH:10][CH:11]=[CH:12][CH:13]=[CH:14][C:5]=12)(=O)[CH3:2].Cl.C([BH3-])#N.[Na+]>CO.C(OCC)C.[Na+].[Cl-].O>[CH2:1]([C:4]1[C:8](=[O:9])[NH:7][C:6]2=[CH:10][CH:11]=[CH:12][CH:13]=[CH:14][C:5]=12)[CH3:2]

Participants

8

Reactant 3

HCID 313Hydrochloric Acid2×HCID 5003444Sodium cyanoborohydrideHCID 10352434HCID 10352434, compound

Product 1

HCID 12852675HCID 12852675, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 5234Sodium ChlorideSolvent

Procedure

3-Acetyl-1,2-dihydrocyclohepta[b]pyrrol-2-one (5.6 g) was suspended in methanol (15 ml). A saturated solution of dry HCl in diethyl ether (10 ml) was added to the suspension. Sodium cyanoborohydride (11.3 g) was gradually added to the suspension which was maintained acidic by the simultaneous addition of more of the HCl solution. The reaction mixture was diluted with a saturated solution of NaCl in water and extracted with ethyl acetate. The extract was dried (Na2SO4) and evaporated to dryness. The residue was dissolved in chloroform and poured through a column of silica gel. Elution of the column with chloroform-methanol (98:2) gave 3-ethyl-1,2-dihydrocyclohepta[b]pyrrol-2-one; mp 166°-171° C.; nmr (CDCl3) δ1.2 (t, J=7 Hz, 3H), 2.65 (q, J=7 Hz, 2H), 7.1 (m, 5H), 12.0 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried (Na2SO4)
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in chloroform
  5. additionpoured through a column of silica gel
  6. washElution of the column with chloroform-methanol (98:2)

Sources & evidence

ORD record
ord-9d5b5695a1eb4da49f38ea270c320f0e
Source dataset
uspto-grants-1982_06
Patent number
US04337265

Reaction notes

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