Water → HCID 13771601, compound

HRID 867394Notes

Reaction equation

HRID 867394 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[C:3]=1[CH2:19][CH2:20][CH2:21][CH2:22][OH:23].BrBr.N12CCCN=C1CCCCC2.O>C(Cl)(Cl)Cl>[C:12]1([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][N:7]=3)[C:2](=[O:1])[C:3]3([CH2:19][CH2:20][CH2:21][CH2:22][O:23]3)[C:4]2=[O:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 547315534-Hydroxy-3-(4-hydroxybutyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 13771601HCID 13771601, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A suspension of 4-Hydroxy-3-(4-hydroxybutyl)-1-phenyl-(1,8)-naphthyridin-2(1H)-one (2 g.) in chloroform was stirred in an ice-bath. A solution of bromine (1 g.) in chloroform was added dropwise and the mixture was stirred overnight at room temperature. To this mixture was added a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (2 g) in chloroform at room temperature. After about 3/4 hr. water was added and the pH was adjusted to be slightly acidic. The chloroform layer was separated and washed with saturated NaCl solution. The solution was dried and evaporated to a solid which was washed with ethanol/water and dried to yield 1-phenyl-3',4', 5', 6'-tetrahydro-spiro[1,8-naphthyridine-3,2'-(2H) pyran]-2,4-dione, m.p. 213°-215° C.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. waitAfter about 3/4 hr
  3. customThe chloroform layer was separated
  4. washwashed with saturated NaCl solution
  5. customThe solution was dried
  6. customevaporated to a solid which
  7. washwas washed with ethanol/water
  8. customdried

Sources & evidence

ORD record
ord-871a73997e724efe920fd99dc4431fdf
Source dataset
uspto-grants-1988_10
Patent number
US04775524

Reaction notes

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