Hydrochloric Acid → HCID 19434244, compound

HRID 1769169Notes

Reaction equation

HRID 1769169 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[C:15]([C:17]([O:19]CC)=[O:18])[N:16]=2)[N:13]=1.[OH-].[Na+].O.Cl>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[C:15]([C:17]([OH:19])=[O:18])[N:16]=2)[N:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 19434250HCID 19434250, compound

Product 1

HCID 19434244HCID 19434244, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of stage (a) (1.94 g, 5 mmol) was heated under reflux with stirring with sodium hydroxide solution (1 ml, 10M, 10 mmol), water (9 ml) and methanol (5 ml) for 20 min. The mixture was cooled and acidified with dilute hydrochloric acid and filtered to give a solid which was dried at 60° in vacuo to give the title compound as a powder (1.5 g), m.p. 224°-226° (decomp), Nmr δH (d6 -DMSO) 8.56 (1H,s,3H), 8.07 (1H,JAB 8.8 Hz, 8H), 7.05 (1H, JAB 8.8 Hz, 7H) 6.88 (2H,s,ArH), 5.29 (2H,s,CH2Ar), 3.82 (6H, s, OCH3)3.68 (3H, s, OCH3) and 3.32 (1H, br.s, CO2H).

Workup

  1. temperatureunder reflux
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customto give a solid which
  5. customwas dried at 60° in vacuo

Sources & evidence

ORD record
ord-911200b067114d10897563f1a40a5ae2
Source dataset
uspto-grants-1995_01
Patent number
US05380759

Reaction notes

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