2-Morpholin-4-yl-8-(1-nitro-dibenzofuran-4-yl)-1-benzopyran-4-one → 8-(1-Amino-dibenzofuran-4-yl)-2-morpholin-4-yl-1-benzopyran-4-one

HRID 641203Notes

Reaction equation

HRID 641203 reaction equation
[N:1]1([C:7]2[O:8][C:9]3[C:17]([C:18]4[C:23]5[O:24][C:25]6[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=6[C:22]=5[C:21]([N+:31]([O-])=O)=[CH:20][CH:19]=4)=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>C(O)(=O)C.[OH-].N.[Zn]>[NH2:31][C:21]1[C:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[O:24][C:23]=2[C:18]([C:17]2[C:9]3[O:8][C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:12][C:11](=[O:13])[C:10]=3[CH:14]=[CH:15][CH:16]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 1

HCID 587571622-Morpholin-4-yl-8-(1-nitro-dibenzofuran-4-yl)-1-benzopyran-4-one

Product 1

HCID 251722678-(1-Amino-dibenzofuran-4-yl)-2-morpholin-4-yl-1-benzopyran-4-oneYield 75%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 21862953Ammonia hydroxideSolvent

Procedure

To a solution of 2-morpholin-4-yl-8-(1-nitro-dibenzofuran-4-yl)-1-benzopyran-4-one (32, 2.5 mmol, 1.11 g) in acetic acid (50 ml) was added zinc dust (25 mmol, 1.64 g), portionwise over ten minutes. The mixture was then stirred at room temperature for 2 hrs, whereupon it was filtered through a Celite™ pad which was washed with methanol (20 ml) and CH2Cl2 (20 ml). Solvents were removed in vacuo to give a slurry which was then diluted with ammonia hydroxide (30 ml) and the resulting solid removed by filtration. The residue was purified by flash chromatography (SiO2) using MeOH; CH2Cl2-1:99 as eluent to give the desired product (75%) in analytically pure form. m/z 413.5 [M+H]+ (Rt=4.27 min).

Workup

  1. waitportionwise over ten minutes
  2. filtrationwas filtered through a Celite™ pad which
  3. washwas washed with methanol (20 ml) and CH2Cl2 (20 ml)
  4. customSolvents were removed in vacuo
  5. customto give a slurry which
  6. customthe resulting solid removed by filtration
  7. customThe residue was purified by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-130dec9d0ef6412584f28cd46eb549f0
Source dataset
uspto-grants-2010_04
Patent number
US07696203B2

Reaction notes

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