Formaldehyde → HCID 17985687, compound

HRID 557233Notes

Reaction equation

HRID 557233 reaction equation
[CH:1]1([C:13]2[C:14](=[O:29])[NH:15][C:16](=[O:28])[C:17]=2[C:18]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:19]=2[CH:20]=[CH:21][N:22]=[CH:23]3)[C:10]2[C:5]3=[C:6]([CH2:11][CH2:12][N:4]3[CH:3]=[N:2]1)[CH:7]=[CH:8][CH:9]=2.[CH2:30]=O.[OH-].[Na+]>CN(C)C=O.C(O)(=O)C>[CH3:30][CH:12]1[N:4]2[C:5]3[C:10]([CH:1]([C:13]4[C:14](=[O:29])[NH:15][C:16](=[O:28])[C:17]=4[C:18]4[CH:27]=[CH:26][CH:25]=[C:24]5[C:19]=4[CH:20]=[CH:21][N:22]=[CH:23]5)[N:2]=[CH:3]2)=[CH:9][CH:8]=[CH:7][C:6]=3[CH2:11]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 67338984HCID 67338984, compound

Product 1

HCID 17985687HCID 17985687, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Add a solution of 3-(5,6-dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-yl)-4-(isoquinolin-5-yl)-2,5-dioxopyrrole (0.300 g, 0.7853 mmol) in anhydrous dimethylformamide (1.5 mL) to formalin (37% solution in water, 0.750 ml) in 2 ml glacial acetic acid and stir at 65° C. for 2 hours. Pour into ice water and neutralize with 5.0N sodium hydroxide. Extract with 200 mL ethyl acetate, wash sequentially with water (1×75 mL), and saturated aqueous sodium chloride (1×75 mL), dry over anhydrous magnesium sulfate, and concentration under reduced pressure. Dissolve the residue in 150 ml 2.0 M ammonia in methanol stir at room temperature for 2 hours, concentrate and purify by column chromatography to give the title compound as an orange solid.

Workup

  1. extractionExtract with 200 mL ethyl acetate
  2. washwash sequentially with water (1×75 mL), and saturated aqueous sodium chloride (1×75 mL)
  3. dry with materialdry over anhydrous magnesium sulfate, and concentration under reduced pressure
  4. dissolutionDissolve the residue in 150 ml 2.0 M ammonia in methanol
  5. stirringstir at room temperature for 2 hours
  6. concentrationconcentrate
  7. custompurify by column chromatography

Sources & evidence

ORD record
ord-b69543a769b4442dba76d547175ac684
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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