Hydrochloric Acid → HCID 178440976, compound

HRID 1057761Notes

Reaction equation

HRID 1057761 reaction equation
[CH2:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](N)=[O:10])=[C:7]([OH:14])[N:6]=1)[CH2:2][CH:3]=[CH2:4].Cl.[OH-:16].[K+]>>[CH2:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:16])=[O:10])=[C:7]([OH:14])[N:6]=1)[CH2:2][CH:3]=[CH2:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 178440937HCID 178440937, compound

Product 1

HCID 178440976HCID 178440976, compoundYield 92%

Procedure

A solution of b1 (12.38 g, 70.1 mmol) in 10% aqueous KOH (350 mL) was heated to reflux for 20 h and subsequently cooled to room temperature. The reaction mixture was acidified with 12 M HCl to pH 2-3, and the resulting precipitate was filtered, washed with water (2×50 mL), and dried under vacuum to afford c1 as a yellow solid (12.46 g, 92%): mp=151-155° C.; IR(cm−1) 2905 (br), 1736, 1652; 1H NMR (DMSO-d6) δ 2.34-2.29(m, 2H), 2.73 (t, 2H, J=7.6), 4.96-5.07 (m, 2H), 5.72-5.85 (m, 1H), 6.56 (d, 1H, J=7.5), 8.28 (d, 1H, J=7.5), 13.26 (s, br, 1H), 14.64 (s, br, 1H); Anal. C10H11NO3·0.10H2O: C, H, N.

Workup

  1. temperatureto reflux for 20 h
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water (2×50 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1b9602f8e7e141b69c9ae68a9bcb8117
Source dataset
uspto-grants-2003_02
Patent number
US06514997B2

Reaction notes

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