Ammonium cerium-nitrate → (+/-) 9-Amino-2-pyridin-4-yl-5,6,8,9-tetrahydro-7-oxa-1,4a-diaza-benzocyclohepten-4-one

HRID 1886969Notes

Reaction equation

HRID 1886969 reaction equation
COC1C=CC(C[NH:8][CH:9]2[C:15]3=[N:16][C:17]([C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=4)=[CH:18][C:19](=[O:20])[N:14]3[CH2:13][CH2:12][O:11][CH2:10]2)=CC=1.[N+]([O-])([O-])=O.[Ce].[NH4+]>C(#N)C.O>[NH2:8][CH:9]1[C:15]2=[N:16][C:17]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[CH:18][C:19](=[O:20])[N:14]2[CH2:13][CH2:12][O:11][CH2:10]1

Participants

4

Reactant 2

HCID 57418452Ammonium cerium-nitrateHCID 668461339-(4-Methoxy-benzylamino)-2-pyridin-4-yl-5,6,8,9-tetrahydro-7-oxa-1,4-a-diaza-benzocyclohepten-4-one

Product 1

HCID 66846193(+/-) 9-Amino-2-pyridin-4-yl-5,6,8,9-tetrahydro-7-oxa-1,4a-diaza-benzocyclohepten-4-one

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of 2.00 g (1.32 mmol) of 9-(4-methoxy-benzylamino)-2-pyridin-4-yl-5,6,8,9-tetrahydro-7-oxa-1,4-a-diaza-benzocyclohepten-4-one in acetonitrile/water (20/10 mL) was added 2.17 g (3.96 mmol) of ammonium cerium nitrate. The reaction was stirred at room temperature for 15 hours. After an acido-basic work-up and extraction with dichloromethane, the organic phase was washed with a saturated solution of sodium chloride, dried over sodium sulphate and concentrated. The crude product was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/aqueous ammonia solution (29%) in the proportions 98/2/0.2 to give 0.226 g (5%, 3 steps) of product as a white powder.

Workup

  1. extractionAfter an acido-basic work-up and extraction with dichloromethane
  2. washthe organic phase was washed with a saturated solution of sodium chloride
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/aqueous ammonia solution (29%) in the proportions 98/2/0.2
  6. customto give 0.226 g (5%, 3 steps) of product as a white powder

Sources & evidence

ORD record
ord-a4ebe43839ca457abe9c6218ad59de3e
Source dataset
uspto-grants-2013_08
Patent number
US08501728B2

Reaction notes

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