Hydrochloric Acid → (5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-acetic acid methyl ester 2HCl

HRID 1808341Notes

Reaction equation

HRID 1808341 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[N:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH2:11][N:12]2C(OC(C)(C)C)=O)=[CH:7][CH:6]=1.[ClH:23]>CO>[ClH:23].[N:14]1[C:13]2[NH:12][CH2:11][CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][C:5]=1[CH2:4][C:3]([O:2][CH3:1])=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 26596924tert-Butyl 7-(2-methoxy-2-oxoethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate

Product 1

HCID 44890895(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-acetic acid methyl ester 2HClYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

tert-Butyl 7-(2-methoxy-2-oxoethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate (1 eq.) (CAS [925889-81-2], available commercially from Fluorochem, for example) was dissolved in methanol (1.6 ml); hydrogen chloride in methanol (1.25 M, 5 equiv.) was added, and the mixture was heated to boiling temperature. After 1 h, the solvent was removed in vacuo and the residue so obtained was used directly in the following stage. Yield: >99%

Workup

  1. temperaturethe mixture was heated
  2. customthe solvent was removed in vacuo
  3. customthe residue so obtained

Sources & evidence

ORD record
ord-783a49abfc89459f9b6501126698b1bf
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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