Hydrochloric Acid → HCID 71075672, compound

HRID 2283185Notes

Reaction equation

HRID 2283185 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([OH:20])[C:11]([NH:14][CH2:15][C:16]([O:18]C)=[O:17])=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].Cl>O1CCCC1.CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([OH:20])[C:11]([NH:14][CH2:15][C:16]([OH:18])=[O:17])=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86674623HCID 86674623, compound

Product 1

HCID 71075672HCID 71075672, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a 50 mL flask is charged methyl {[5-(3-chlorophenyl)-3-hydroxypyridin-2-yl]amino}-acetate, 4, (0.45 g, 1.4 mmol), tetrahydrofuran (4.5 mL) and 1 M NaOH (4.5 mL, 4.5 mmol). The mixture was stirred for 2 hours at room temperature after which it was determined by TLC analysis using hexane/ethyl acetate (6:3) as the mobile phase and UV 435 nm to visualize the reaction components that the reaction was complete. The reaction solution was adjusted to pH 1 with concentrated HCl and the solution was heated at 35° C. under vacuum until all of the tetrahydrofuran had been removed. A slurry forms as the solution is concentrated. With efficient stirring the pH is adjusted to ˜2 with the slow addition of 1 M NaOH. The solid which forms was collected by filtration, washed with water, followed by hexane, then dried under vacuum to afford 0.38 g (88% yield) of the desired product as a white solid. 1H NMR (DMSO-d6) δ 12.84 (s, 1H), 12.39 (s, 1H), 9.39 (t, 1H), 8.56 (d, 1H), 7.94 (s, 1H), 7.81 (m, 2H), 7.55 (q, 2H), and 4.02 (d, 2H).

Workup

  1. customthe reaction components that the reaction
  2. customhad been removed
  3. concentrationA slurry forms as the solution is concentrated
  4. stirringWith efficient stirring the pH
  5. additionis adjusted to ˜2 with the slow addition of 1 M NaOH
  6. filtrationThe solid which forms was collected by filtration
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-033d3f9979544dbd997ff4203ae3f09a
Source dataset
uspto-grants-2015_09
Patent number
US09145366B2

Reaction notes

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