Hydrochloric Acid → HCID 89500349, compound

HRID 925470Notes

Reaction equation

HRID 925470 reaction equation
[CH3:1][N:2](C)/C=N/[H].[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH3:21])[C:15]([C:18]([OH:20])=O)=[N:16][CH:17]=1.CC([O-])(C)C.[K+].Cl>C1COCC1>[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[N:16][C:15]2[C:18](=[O:20])[NH:2][CH:1]=[CH:21][C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 178496170HCID 178496170, compound

Product 1

HCID 89500349HCID 89500349, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-(2-Methoxy-ethoxy)-3-methyl-pyridine-2-carboxylic acid 1-dimethylamino-meth-(E)-ylideneamine (500 mg, 1.885 mmol) was dissolved in THF (15 ml) and heated to gentle reflux. KOtBu (317 mg, 2.83 mmol) in THF (30 ml) was added dropwise and the reaction mixture was heated to reflux for 2.5 h and then cooled to rt. The pH was adjusted to 7 with concentrated HCl. The reaction mixture was concentrated.

Workup

  1. temperatureheated to gentle reflux
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 2.5 h
  4. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-f0b7a8a5f65e49578a73a5aa22f0fd78
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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