Hydrochloric Acid → HCID 13823460, compound

HRID 1906417Notes

Reaction equation

HRID 1906417 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:7](=[O:23])[N:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[CH:11][N:10]=2.C(N(CC)CC)C.O.Cl>C(Cl)Cl>[C:17]1([N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][N:10]=3)[C:15](=[O:16])[C:6]3([CH2:5][CH2:4][CH2:3][CH2:2]3)[C:7]2=[O:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 547165513-(4-Bromobutyl)-4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 13823460HCID 13823460, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 3-(4-bromobutyl)-4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)one (5 g.) in methylene chloride (350 ml.), in an atmosphere of nitrogen, was stirred at room temperature and to it was added triethylamine (4.1 ml.). The mixture was stirred at room temperature for 16 hrs. Water (300 ml.) was added and the aqueous layer was adjusted to pH 4.5 with hydrochloric acid. The organic layer was separated and the aqueous layer was back-extracted with methylene chloride. The combined organic layers were washed with water, dried (Na2SO4), filtered and evaporated to yield a solid which was recrystallized from isopropanol to yield 1'-phenylspiro[cyclopentane-1,3'-(1,8)naphthyridine]-2',4'-(1'H)dione, m.p. 178°-179° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 16 hrs
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was back-extracted with methylene chloride
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a solid which
  9. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-2803ec2b84e84f48a7995f6aa0119183
Source dataset
uspto-grants-1987_03
Patent number
US04652564

Reaction notes

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