HCID 178469475, compound → HCID 178469472, compound

HRID 745944Notes

Reaction equation

HRID 745944 reaction equation
C(OC([N:11]1[CH2:20][CH2:19][C:18]2[N:17]=[CH:16][C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:14]([OH:26])[C:13]=2[CH2:12]1)=O)C1C=CC=CC=1>[Pd].C(O)(=O)C>[OH:26][C:14]1[C:13]2[CH2:12][NH:11][CH2:20][CH2:19][C:18]=2[N:17]=[CH:16][C:15]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

4

Reactant 1

HCID 178469475HCID 178469475, compound

Product 1

HCID 178469472HCID 178469472, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

The starting material is prepared as follows: Ethyl 6-benzyloxycarbonyl-4-hydroxy-5,6,7,8-tetrahydro[1,6]naphthyridine-3-carboxylate (Example 1i) is hydrogenated with palladium on carbon as the catalyst in glacial acetic acid to obtain ethyl 4-hydroxy-5,6,7,8-tetrahydro[1,6]naphthyridine-3-carboxylate, which is treated with benzyl bromide in a mixture of triethylamine and DMF at 60° for 48 hr to obtain ethyl 6-benzyl-4-hydroxy-5,6,7,8-tetrahydro[1,6]naphthyridine-3-carboxylate. Treatment of this material with an excess of phosphorous oxychloride at reflux for 5 hr affords the required ethyl 6-benzyl-4-chloro-5,6,7,8-tetrahydro[1,6]naphthyridine-3-carboxylate.

Workup

  1. customThe starting material is prepared

Sources & evidence

ORD record
ord-0bd884ac26e541a2985ca7e90f855bf3
Source dataset
uspto-grants-1986_07
Patent number
US04602014

Reaction notes

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