Formaldehyde → HCID 86756251, compound

HRID 279037Notes

Reaction equation

HRID 279037 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 mol) 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-4fb7bddbb0554990a46c2c885c4b65ed
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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