Ammonia → 4-Ethyl-7-(4-nitro-phenylazo)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ol

HRID 1190779Notes

Reaction equation

HRID 1190779 reaction equation
F[B-](F)(F)F.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]#[N:16])=[CH:11][CH:10]=1)([O-:8])=[O:7].[CH2:17]([N:19]1[C:24]2[CH:25]=[C:26]([OH:29])[CH:27]=[CH:28][C:23]=2[O:22][CH2:21][CH2:20]1)[CH3:18].N>S(=O)(=O)(O)O>[CH2:17]([N:19]1[C:24]2[CH:25]=[C:26]([OH:29])[C:27]([N:16]=[N:15][C:12]3[CH:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:14][CH:13]=3)=[CH:28][C:23]=2[O:22][CH2:21][CH2:20]1)[CH3:18]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 680064-Nitrobenzenediazonium tetrafluoroborateHCID 687776134-Ethyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ol

Product 1

HCID 1363315334-Ethyl-7-(4-nitro-phenylazo)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

p-Nitrobenzenediazonium tetrafluoroborate (0.251 g, 1.06 mmol) was dissolved in 10% sulfuric acid (10 ml) and added to a methanolic solution (10 ml) of 50a (0.19 g, 1.06 mmol). The solution turned red immediately. The reaction mixture was neutralized with ammonia. The red precipitate was filtered to give quantitative yield of the product. ES-HRMS [M−H]− 327.1428. Calcd for (C16H15N4O4): 327.1094.

Workup

  1. filtrationThe red precipitate was filtered

Sources & evidence

ORD record
ord-3f8f00a583894ec9a8897db4f9fb689d
Source dataset
uspto-grants-2014_03
Patent number
US08679776B2

Reaction notes

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