2-(6-Methoxypyridin-2-yl)ethan-1-amine → HCID 178470231, compound

HRID 2202235Notes

Reaction equation

HRID 2202235 reaction equation
C[O:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][NH2:11])[CH:6]=[CH:5][CH:4]=1.[ClH:12].COC1CCCC1.[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[CH:21]=O.C1(C)C=CC=CC=1>CCO>[ClH:12].[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:21]([C:20]([O:24][CH2:25][CH3:26])=[O:23])[NH:11][CH2:10][CH2:9][C:7]=2[N:8]=1

Participants

5

Reactant 3

HCID 212435192-(6-Methoxypyridin-2-yl)ethan-1-amineHCID 66926893hydrogen chloride CPME2×HCID 86599969Ethyl glyoxylate toluene2×

Product 1

HCID 178470231HCID 178470231, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(6-methoxypyridin-2-yl)ethanamine (14.43 g, 94.81 mmol), 4N hydrogen chloride/CPME (26.1 mL, 104.29 mmol) and 47% ethyl glyoxylate/toluene solution (polymer form) (30.0 mL, 142.22 mmol) in EtOH (175 mL) was heated under reflux for 8 hr. To the reaction mixture were added 4N hydrogen chloride/CPME (26.1 mL, 104.29 mmol) and 47% ethyl glyoxylate/toluene solution (polymer form) (30.0 mL, 142.22 mmol), and the mixture was heated again under reflux for 16 hr. The reaction mixture was concentrated under reduced pressure to half volume, and to the residue was added diethyl ether (ca. 150 mL). The precipitate was collected by filtration, and washed with EtOH/diethyl ether to give crude ethyl 2-hydroxy-5,6,7,8-tetrahydro-1,6-naphthyridine-5-carboxylate hydrochloride (20.01 g, 77 mmol, 82%) as an off-white powder.

Workup

  1. temperatureunder reflux for 8 hr
  2. temperaturethe mixture was heated again
  3. temperatureunder reflux for 16 hr
  4. concentrationThe reaction mixture was concentrated under reduced pressure to half volume
  5. additionto the residue was added diethyl ether (ca. 150 mL)
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with EtOH/diethyl ether

Sources & evidence

ORD record
ord-8147c7eedd4e41ee8e937e2a4ff624a3
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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