HCID 54710160, compound → HCID 54710186, compound

HRID 1598551Notes

Reaction equation

HRID 1598551 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-7a72a962545d4b4e9f5b8396ce6cdb72
Source dataset
uspto-grants-1998_04
Patent number
US05739130

Reaction notes

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