Formaldehyde → HCID 22624037, compound

HRID 279036Notes

Reaction equation

HRID 279036 reaction equation
[OH:1][N:2]1[C:11](=[O:12])[C:10]2[CH:13]=[C:14]([OH:17])[C:15](Br)=[C:8]3[C:9]=2[C:4](=[CH:5][CH:6]=[CH:7]3)[C:3]1=[O:18].C=O.CN.[CH2:23]([N:25](CC)[CH2:26]C)C>O1CCOCC1>[OH:1][N:2]1[C:3](=[O:18])[C:4]2[C:9]3[C:8]([CH:7]=[CH:6][CH:5]=2)=[C:15]2[N:25]([CH3:26])[CH2:23][O:17][C:14]2=[CH:13][C:10]=3[C:11]1=[O:12]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6329MethylamineHCID 8471TriethylamineHCID 22623894HCID 22623894, compound

Product 1

HCID 22624037HCID 22624037, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 175 mg (0.57 mmol) of 2,5-dihydroxy-6-bromo-benzo[de]isoquinoline-1,3-dione (from Example 125) in 4 mL dioxane was added 0.6 mL (22 mmol) of 37% aqueous formaldehyde, 0.2 mL (2.32 mmol) of 40% aqueous methylamine, and 0.078 mL (0.57 mmol) of triethyl amine. The reaction mixture was stirred at room temperature for 220 hours and quenched with 20 mL water. The precipitate was isolated, washed with water, and dried to yield 50 mg of the title compound, mp 263-265° C.

Workup

  1. customquenched with 20 mL water
  2. customThe precipitate was isolated
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-7ec13ef466b34eb284faf0263a1a9121
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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