Hydrochloric Acid → HCID 9801985, compound

HRID 1004209Notes

Reaction equation

HRID 1004209 reaction equation
C[O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[C:14](=[O:32])[NH:15][C:16](=[O:31])[C:17]=2[C:18]2[C:26]3[C:21](=[CH:22][C:23]([N+:27]([O-:29])=[O:28])=[CH:24][CH:25]=3)[N:20]([CH3:30])[CH:19]=2)=[CH:5]1.Cl>C1COCC1>[OH:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[C:14](=[O:32])[NH:15][C:16](=[O:31])[C:17]=2[C:18]2[C:26]3[C:21](=[CH:22][C:23]([N+:27]([O-:29])=[O:28])=[CH:24][CH:25]=3)[N:20]([CH3:30])[CH:19]=2)=[CH:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18794870HCID 18794870, compound

Product 1

HCID 9801985HCID 9801985, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 727.5 mg of 3-[1-(methoxymethyl)-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indole-3-yl)-pyrrole-2,5-dione (11) from Step F above in 65 ml of THF was treated with approximately 40 ml of 2N-HCl. The reaction mixture was refluxed for 5 hours, cooled and the product was extracted with ethyl acetate. The organic phase was dried on MgSO4 and the solvent evaporated to give an orange solid. Chromatographic purification of this material yielded 123.3 mg of 3-(1-hydroxymethyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (II) as a red solid, mp 210-213° C. MS: (M+), m/z 416.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. temperaturecooled
  3. extractionthe product was extracted with ethyl acetate
  4. customThe organic phase was dried on MgSO4
  5. customthe solvent evaporated
  6. customto give an orange solid
  7. customChromatographic purification of this material

Sources & evidence

ORD record
ord-d804c770d2ed4626bb95edcadb843a27
Source dataset
uspto-grants-2000_04
Patent number
US06048887

Reaction notes

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