tert-butyl (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylate → (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid Hydrochloride

HRID 18258

Reaction equation

HRID 18258 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[CH:8][C:7](/[CH:12]=[CH:13]/[C:14]([O:16]C(C)(C)C)=[O:15])=[CH:6][C:5]=2[CH2:4][CH2:3]1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:29]>>[ClH:29].[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[CH:8][C:7](/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])=[CH:6][C:5]=2[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 10869488tert-butyl (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylateHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid HydrochlorideYield 100%

Procedure

To tert-butyl (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylate (7.0 g, 25.5 mmole) was added 1:1 TFA/CH2Cl2 (100 mL). The reaction was stirred for 30 min, then was concentrated under vacuum. The residue was suspended in 4 N HCl/dioxane (100 mL), triturated, and concentrated to dryness. The resulting solid was triturated with Et2O, collected, and dried under vacuum to give the title compound (6.55 g, 100%) as a off-white solid: 1H NMR (400 MHz, d6-DMSO) δ 10.72 (s, 1 H), 8.35 (d, J=2.0 Hz, 1 H), 8.04 (s, 1H), 7.54 (d, J=16.0 Hz, 1 H), 6.51 (d, J=16.0 Hz, 1 H), 2.91 (t, 2 H), 2.53 (t, 2 H); MS (ES) m/e 219.0 (M+H)+.

Workup

  1. concentrationwas concentrated under vacuum
  2. customtriturated
  3. concentrationconcentrated to dryness
  4. customThe resulting solid was triturated with Et2O
  5. customcollected
  6. customdried under vacuum

Sources & evidence

ORD record
ord-36d612f86097443db6c2786d21e863b2
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Linked notes

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