Hydrochloric Acid → HCID 136347711, compound

HRID 1866465Notes

Reaction equation

HRID 1866465 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7]([CH:15]=[CH:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[N:21][CH:22]=2)[CH:8]=[CH:9][C:10]=1[O:11]COC.Cl.O.[OH-].[Na+]>CO>[OH:4][C:5]1[CH:6]=[C:7]([CH:15]=[CH:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[N:21][CH:22]=2)[CH:8]=[CH:9][C:10]=1[OH:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water3×HCID 14798Sodium HydroxideHCID 68976207HCID 68976207, compound

Product 1

HCID 136347711HCID 136347711, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 5-{2-[3,4-bis(methoxymethoxy)phenyl]vinyl}-[2,2′]bipyridinyl (0.85 g, 2.246 mmol), concentrated hydrochloric acid (5 mL) and water (2 mL) in methanol (100 mL) was stirred under argon atmosphere at room temperature for 15 hoursw. Water (50 mL) was added to the mixture and methanol was rotary evaporated. More water (100 mL) was added and the resulting mixture was neutralized to pH 7 with sodium hydroxide solution. The solid precipitate was collected by filtration and washed with water and a mixed solvent of hexane and EtOAc (3:1, v/v). The resulting orange solid was dried under high vacuum giving 0.5559 g of 5-{2-[3,4-dihydroxyphenyl]vinyl}-[2,2′]bipyridinyl (1.915 mmol, yield 85.3%) as a Z/E mixture. 1H NMR (MeOH, 300.16 MHz): 8.71 (d, J=1.7 Hz, 0.70H), 8.65-8.62 (m, 1.56H), 8.51 (d, J=1.4 Hz, 1.03H), 8.31-8.23 (m, 2.29H), 8.16 (d, J=8.3 Hz, 1.00H), 8.0 (dd, J=2.0 Hz, 0.78H), 7.94-7.89 (m, 1.63H), 7.80 (dd, J=8.2 & 2.0 Hz, 1.04H), 7.44-7.40 (m, 1.52H), 7.23 (d, J=16.4 Hz, 0.74H), 7.08 (d, J=1.8 Hz, 0.71H), 7.00 (d, J=16.4 Hz, 0.74H), 6.95 (dd, J=8.2 & 1.8 Hz, 0.70H), 6.77 (d, J=8.2 Hz, 0.74H), 6.72-6.67 (m, 2.80H), 6.61 (dd, J=8.1 & 1.5 Hz, 1.01H), 6.47 (d, J=12.1 Hz, 1.00H). UV-Vis (MeOH): Emax=252 nm, 288 nm and 352 nm. MS (ESI) m/z: 291 (M+1)+.

Workup

  1. filtrationThe solid precipitate was collected by filtration
  2. washwashed with water
  3. customThe resulting orange solid was dried under high vacuum

Sources & evidence

ORD record
ord-71e29d620c6d4c67ae11eb2fcc4c4bb0
Source dataset
uspto-grants-2009_12
Patent number
US07629375B2

Reaction notes

Loading…