Sodium Hydroxide → HCID 67078752, compound

HRID 1295791Notes

Reaction equation

HRID 1295791 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]([OH:11])=O)[CH:2]=1.[OH-].[Na+].[NH2:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]([NH:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:23][CH:24]=2)=[O:11])[CH:2]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 655264-(Aminomethyl)Benzoic AcidHCID 1019843-(3-Pyridinyl)-2-propenoic acid

Product 1

HCID 67078752HCID 67078752, compoundYield 82%

Procedure

To a suspension of 0.33 g (2.01 mmol) of N,N′-carbonyldiimidazole in tetrahydrofunan (10 ml) is added drop-wise a solution of 0.30 g (2.01 mmol) of 3-pyridineacrylic acid at 0° C. Then, the mixture is stirred at room temperature for 3 hours and added drop-wise to a separately prepared 2.0 ml (2.00 mmol) of 1N aqueous sodium hydroxide solution including 0.30 g (2.00 mmol) of 4-aminomethylbenzoic acid, followed by stirring at room temperature for 8 hours. The reaction mixture is evaporated under vacuum. To the residue is added a saturated solution of sodium chloride (2 ml), then the mixture is neutralized with concentrated hydrochloric acid to pH 5. The deposited white solid is collected by filtration, washed with ice-water, and then dried to give the title compound (0.46 g, 82%). HRMS calcd for C16H14N2O3: 282.2988. Found: 282.2990. MA calcd for: C16H14N2O3: C, 68.07%; H, 5.00%; N, 9.92%. Found: C, 68.21%; H, 5.03%; N, 9.90%.

Workup

  1. stirringby stirring at room temperature for 8 hours
  2. customThe reaction mixture is evaporated under vacuum
  3. additionTo the residue is added a saturated solution of sodium chloride (2 ml)
  4. filtrationThe deposited white solid is collected by filtration
  5. washwashed with ice-water
  6. customdried

Sources & evidence

ORD record
ord-781ed6bc3fda4d71915d0879ebb02e15
Source dataset
uspto-grants-2007_07
Patent number
US07244751B2

Reaction notes

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