Water → 13-Amino-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano-[3,2-h]acridin-7-one

HRID 478692Notes

Reaction equation

HRID 478692 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[O:29][C:28]([CH3:31])([CH3:30])[CH:27]=[CH:26][C:6]2=[C:7]2[C:16]=1[C:15](=[O:17])[C:14]1[CH:13]=[C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]3=[C:10]([N+:22]([O-])=O)[C:9]=1[N:8]2[CH3:25].O>C(O)(=O)C.[Zn]>[NH2:22][C:10]1[C:9]2[N:8]([CH3:25])[C:7]3[C:16](=[C:3]([O:2][CH3:1])[CH:4]=[C:5]4[O:29][C:28]([CH3:30])([CH3:31])[CH:27]=[CH:26][C:6]4=3)[C:15](=[O:17])[C:14]=2[CH:13]=[C:12]2[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=12

Participants

5

Reactant 2

HCID 962WaterHCID 220645286-Methoxy-3,3,14-trimethyl-13-nitro-3,14-dihydro-7H-benzo[b]pyrano-[3,2-h]acridin-7-one

Product 1

HCID 1023744413-Amino-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano-[3,2-h]acridin-7-one

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To 178 mg of the compound obtained in Step 6 above in 10 ml of acetic acid and 1 ml of water there are added 621 mg of zinc wool. The reaction mixture is stirred at ambient temperature for 2.5 hours and is then filtered. The filtrate is made alkaline using 10% aqueous ammonium hydroxide solution; the precipitate formed is then separated off by filtration. The crude residue is purified by chromatography over silica gel (dichloromethane/methanol: gradient from 0.1 to 0.5%), allowing the expected product to be isolated.

Workup

  1. filtrationis then filtered
  2. customthe precipitate formed
  3. customis then separated off by filtration
  4. customThe crude residue is purified by chromatography over silica gel (dichloromethane/methanol: gradient from 0.1 to 0.5%)
  5. customto be isolated

Sources & evidence

ORD record
ord-5c346608a2f64323b9e5020f66abf4a2
Source dataset
uspto-grants-2003_11
Patent number
US06642248B2

Reaction notes

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