Nitrogen → N-(6-nitro-2,3-dihydro-1H-inden-5-yl)acetamide

HRID 1669059Notes

Reaction equation

C(C1N=[N+:5]([O-:16])[C:6]2[CH:15]=[C:14]3[C:10]([CH2:11][CH2:12][CH2:13]3)=[CH:9][C:7]=2[N:8]=1)C.N#N.ClC1N=[N+]([O-:33])C2C=C3C(CCC3)=CC=2N=1.[Sn](CC)(CC)(CC)CC.C[O:44][CH2:45][CH2:46]OC>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N+:5]([C:6]1[CH:15]=[C:14]2[C:10]([CH2:11][CH2:12][CH2:13]2)=[CH:9][C:7]=1[NH:8][C:45](=[O:44])[CH3:46])([O-:16])=[O:33]

Participants

Conditions

Temperature: 85 °C

Procedure

Alternative Preparation of Ethyl-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide (67). Pd(dppf)Cl2 (130 mg, 0.08 mmol) was added under N2 to a N2-purged solution of chloride 21 (350 mg, 1.6 mmol) and SnEt4 (455 mg, 1.9 mmol) in DME (20 mL) and the mixture was stirred at 85° C. for 16 h. The mixture was cooled, the solvent evaporated and the residue purified by chromatography, eluting with 20% EtOAc/pet. ether, to give (i) starting material 21 (148 mg, 42%) and (ii) 1-oxide 67 (84 mg, 25%) as a yellow solid: mp 79-81° C., spectroscopically identical to the sample prepared above.

Workup

temperatureThe mixture was cooled
customthe solvent evaporated
customthe residue purified by chromatography
washeluting with 20% EtOAc/pet. ether

Sources & evidence

ORD record: ord-09a659a891c04074b82287b80d43179b
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989451B2

Reaction notes

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