Hydrochloric Acid → HCID 22139032, compound

HRID 1362096Notes

Reaction equation

HRID 1362096 reaction equation
C([O:5][C:6](=[O:20])/[CH:7]=[CH:8]/[C:9]1[CH:10]=[N:11][C:12]2[NH:13][C:14](=[O:19])[CH2:15][CH2:16][C:17]=2[CH:18]=1)(C)(C)C.[O:21]1CCOCC1.[OH-].[Na+].Cl>CO>[NH2:13][C:12]1[N:11]=[CH:10][C:9](/[CH:8]=[CH:7]/[C:6]([OH:5])=[O:20])=[CH:18][C:17]=1[CH2:16][CH2:15][C:14]([OH:19])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 10869488tert-butyl (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylate

Product 1

HCID 22139032HCID 22139032, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (E)-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylic acid tert-butyl ester (0.86 g, 3.0 mmol) was stirred in methanol (10 mL), dioxane (10 mL) and aq. NaOH (15 mL of a 1 N solution, 15 mmol) for 4 days. The clear solution was neutralized with aq. HCl (15 mL of a 1 N solution, 15 mmol) and stirred for 20 min. The white precipitate was collected by filtration to give (E)-3-[6-amino-5-(2-carboxy-ethyl)pyridin-3-yl]acrylic acid (0.57 g, 78%): MS (ESI) m/e 237 (M+H)+.

Workup

  1. filtrationThe white precipitate was collected by filtration

Sources & evidence

ORD record
ord-4c736e9ac1e3483b9e103a68c01bb903
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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