Formaldehyde → HCID 86756251, compound

HRID 567045Notes

Reaction equation

HRID 567045 reaction equation
[OH:1][N:2]1[C:11](=[O:12])[C:10]2[CH:13]=[C:14]([OH:16])[CH:15]=[C:8]3[C:9]=2[C:4](=[CH:5][CH:6]=[CH:7]3)[C:3]1=[O:17].[CH2:18]=O.[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>O1CCOCC1>[OH:1][N:2]1[C:11](=[O:12])[C:10]2[C:13]([CH3:18])=[C:14]([OH:16])[C:15]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[C:8]3[C:9]=2[C:4](=[CH:5][CH:6]=[CH:7]3)[C:3]1=[O:17]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 4671088HCID 4671088, compound

Product 1

HCID 86756251HCID 86756251, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 150 mg (0.66 mmol) of 2,5-dihydroxy-benzo[de]isoquinoline-1,3-dione (from Example 3) in 4 mL dioxane was added 0.6 mL (7.4 mmol) of 37% aqueous formaldehyde, and then 168 mg (2.0 mmol) of piperidine. The reaction mixture was stirred at room temperature 40 hours and quenched with 25 mL water. The precipitate was isolated, washed with water, and dried to yield 145 mg of the title compounds, mp 224-225° C.

Workup

  1. customquenched with 25 mL water
  2. customThe precipitate was isolated
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-fe407b46b6df4a0490797e679ae01879
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

Loading…