Water → HCID 13934585, compound

HRID 2118683Notes

Reaction equation

HRID 2118683 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][CH:20](O)[CH3:21].N1C=CC=CC=1.O=S(Cl)Cl.O>C(Cl)Cl>[CH3:21][CH:20]1[O:18][C:4]2[N:5]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:6]3[C:11]([C:2](=[O:1])[C:3]=2[CH2:19]1)=[CH:10][CH:9]=[CH:8][N:7]=3

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 547178214-Hydroxy-3-(2-hydroxypropyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 13934585HCID 13934585, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 4-hydroxy-3-(2-hydroxypropyl)1-phenyl-1,8-naphthyridin-2(1H)-one (1 g.) in CH2Cl2 was stirred in an atmosphere of nitrogen. To this was added pyridine (1.5 ml.). To this mixture was added a solution of SOCl2 (1.5 ml.) in CH2Cl2 (10 ml.) dropwise over a period of 15 minutes. The mixture was stirred overnight at room temperature then water was added. The CH2Cl2 layer was separated, dried and evaporated. Recrystallization from isopropanol yielded the product, m.p. 207°-209° C.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customThe CH2Cl2 layer was separated
  3. customdried
  4. customevaporated
  5. customRecrystallization from isopropanol
  6. customyielded the product, m.p. 207°-209° C.

Sources & evidence

ORD record
ord-b99498ad8450448a874b5a8ddb511c93
Source dataset
uspto-grants-1987_07
Patent number
US04680297

Reaction notes

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