Hydrochloric Acid → HCID 66778542, compound

HRID 1847615Notes

Reaction equation

HRID 1847615 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]([C:18]([OH:20])=[O:19])[CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:21].[CH3:22]O>>[ClH:21].[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]([C:18]([O:20][CH3:22])=[O:19])[CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 468398966-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxylic acid

Product 1

HCID 66778542HCID 66778542, compoundYield 100%

Conditions

Temperature
80 °C

Procedure

In a sealed container, 6-benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxylic acid (1.00 g, 3.73 mmol) was dissolved in MeOH (40.0 mL) and HCl (3.29 mL, 14.9 mmol, 4.0 M in 1,4-dioxane). The resulting solution was heated at 80° C. for 13 h. The solvent and acid were completely evaporated to yield methyl 6-benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxylate hydrochloride (1.25 g, 100%). LC-MS: (FA) ES+ 283; 1H NMR (Methanol-d4, 400 MHz) δ8.08 (d, J=8.0 Hz, 1 H), 7.92 (d, J=8.3 Hz, 1 H), 7.63 (m, 2 H), 7.54 (m, 3 H), 4.88 (s, 2 H), 4.58 (s, 4 H), 3.99 (s, 3 H), 3.40 (s, 2 H).

Workup

  1. customThe solvent and acid were completely evaporated

Sources & evidence

ORD record
ord-009f4a43f23e464b91aeaae31cf81538
Source dataset
uspto-grants-2015_02
Patent number
US08952163B2

Reaction notes

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