Hydrochloric Acid → Methyl 5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxylate--hydrogen chloride (1/1)

HRID 1847624Notes

Reaction equation

HRID 1847624 reaction equation
[N:1]1[C:10]2[CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([C:18]([O:20][CH3:21])=[O:19])[CH:2]=1.[ClH:22]>>[ClH:22].[N:1]1[C:10]2[CH2:9][NH:8][CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([C:18]([O:20][CH3:21])=[O:19])[CH:2]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 534464617-tert-Butyl 3-methyl 5,8-dihydro-1,7-naphthyridine-3,7(6H)-dicarboxylate

Product 1

HCID 56847166Methyl 5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxylate--hydrogen chloride (1/1)Yield 119.5%

Procedure

A round-bottom flask containing 7-tert-butyl 3-methyl 5,6-dihydro-1,7-naphthyridine-3,7-(8H)-dicarboxylate (0.470 g, 1.61 mmol) and hydrochloric acid (6.03 mL, 24.1 mmol, 4.0 M in 1,4-dioxane) was stirred at rt for 1 h. The solution was then completely evaporated to yield methyl 5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxylate hydrochloride (0.440 g, 100%). LC-MS: (FA) ES+ 193; 1H NMR (Methanol-d4, 400 MHz) δ9.26 (s, 1 H), 8.87 (s, 1 H), 4.83 (s, 2 H), 4.03 (s, 3 H), 3.69 (m, 2 H), 3.43 (t, J=5.5 Hz, 2 H).

Workup

  1. customThe solution was then completely evaporated

Sources & evidence

ORD record
ord-b5818f8cbbda4632a8a87ba73cbd3cc9
Source dataset
uspto-grants-2015_02
Patent number
US08952163B2

Reaction notes

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