HCID 54710160, compound → HCID 54710186, compound

HRID 1080650Notes

Reaction equation

HRID 1080650 reaction equation
[OH:1][C:2]1[C:11]2[CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=[C:9]3[C:10]=2[N:5]([CH2:6][CH2:7][O:8]3)[C:4](=[O:18])[C:3]=1[C:19]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1)=[O:20]>O1CCCC1.[Pt]=O>[NH2:15][C:13]1[CH:14]=[C:9]2[O:8][CH2:7][CH2:6][N:5]3[C:4](=[O:18])[C:3]([C:19]([N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH2:23][CH2:22]4)=[O:20])=[C:2]([OH:1])[C:11]([CH:12]=1)=[C:10]23

Participants

4

Reactant 1

HCID 54710160HCID 54710160, compound

Product 1

HCID 54710186HCID 54710186, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,3-dihydro-7-hydroxy-9-nitro-6-(1-indolinylcarbonyl)-5-oxo-5H-pyrido [1,2,3-de]-1,4-benzoxazine (2.5 g) and platinum oxide (0.1 g) in tetrahydrofuran (150 ml) was stirred under hydrogen (3 atm.) for 2 hours. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (60 g) eluting with chloroform-methanol (20:1). The desired product was washed with ethanol to give crystals of 2,3-dihydro-9-amino-7-hydroxy-6-(1-indolinylcarbonyl)-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (1.2 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (60 g)
  4. washeluting with chloroform-methanol (20:1)
  5. washThe desired product was washed with ethanol

Sources & evidence

ORD record
ord-af40d77226d44d6294488c31136cbede
Source dataset
uspto-grants-1996_12
Patent number
US05583135

Reaction notes

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