Acetic Acid → HCID 18967735, compound

HRID 399537Notes

Reaction equation

HRID 399537 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH:5]([C:23]#[N:24])[CH2:6][CH:7]1[C:12](=O)[CH2:11][CH2:10][CH:9]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:8]1)[CH3:2].Br.C(O)(=[O:29])C>>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH:9]2[CH2:10][CH2:11][C:12]3[NH:24][C:23](=[O:29])[CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:25])[CH2:6][C:7]=3[CH2:8]2)=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 57025170HCID 57025170, compound

Product 1

HCID 18967735HCID 18967735, compound

Procedure

2-Cyano-3-(3-(4-methoxyphenyl)methyl-6-oxocyclohexanyl)propanoic acid ethyl ester (2.43 g) was added to 15% w/v solution of HBr in acetic acid at 5° C. and stirred for 30 minutes. The reaction mixture was evaporated under reduced pressure and washed with saturated sodium carbonate solution. The mixture was extracted into ethyl acetate and the organic phase dried (MgSO4) and evaporated. The residue was diluted with ether and allowed to crystallise to give ethyl 3,4,5,6,7,8-hexahydro-6-((4-methoxyphenyl)methyl)quinolin-2[1H]-one-3-carboxylate (0.5 g) mp. 143°-145° C.

Workup

  1. customat 5° C.
  2. customThe reaction mixture was evaporated under reduced pressure
  3. washwashed with saturated sodium carbonate solution
  4. extractionThe mixture was extracted into ethyl acetate
  5. dry with materialthe organic phase dried (MgSO4)
  6. customevaporated
  7. additionThe residue was diluted with ether
  8. customto crystallise

Sources & evidence

ORD record
ord-66d01aacab864341bc7099678c59b53e
Source dataset
uspto-grants-1998_10
Patent number
US05821251

Reaction notes

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