Formaldehyde → 2-(hydroxymethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

HRID 435811

Reaction equation

HRID 435811 reaction equation
[CH:1]1[CH:2]=[C:3]2[C:8]3=[C:9]([C:11]([NH:13][C:14](=[O:15])[C:7]3=[CH:6][CH:5]=[CH:4]2)=[O:12])[CH:10]=1.[CH2:16]=[O:17]>CN(C)C=O>[OH:17][CH2:16][N:13]1[C:14](=[O:15])[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]3[C:8]=2[C:9](=[CH:10][CH:1]=[CH:2]3)[C:11]1=[O:12]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 66491Naphthalimide

Product 1

HCID 114135142-(hydroxymethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

30 g. (0.15 mole) of 1,8-naphthalimide and 12.5 ml. of 37% aqueous formaldehyde (0.17 mole) are combined in 100 ml. of dimethylformamide and heated on a hot plate (90°-110°) until all the materials dissolve. The solution is then allowed to stand overnight at 25°. The resulting precipitate is filtered off, washed with water and recrystallized from dioxane. This material is dried overnight at 25° (0.1 mm.) to yield 26.4 g. of the titled compound which has an indistinct melting point.

Workup

  1. dissolutiondissolve
  2. filtrationThe resulting precipitate is filtered off
  3. washwashed with water
  4. customrecrystallized from dioxane
  5. customThis material is dried overnight at 25° (0.1 mm.)
  6. customto yield 26.4 g

Sources & evidence

ORD record
ord-3eab9337358e44f183a0432cc8c51e09
Source dataset
uspto-grants-1977_02
Patent number
US04006238

Linked notes

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