4-Bromoaniline → HCID 67512786, compound

HRID 1037522Notes

Reaction equation

[CH:1]1([C:4]2[C:5]([N+:15]([O-:17])=[O:16])=[CH:6][C:7]([N+:12]([O-:14])=O)=[C:8]([CH:11]=2)[CH:9]=O)[CH2:3][CH2:2]1.[Br:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.[C-:26]#[N:27].[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C>[Br:18][C:19]1[CH:25]=[CH:24][C:22]([N:23]2[C:9]([C:26]#[N:27])=[C:8]3[C:7]([CH:6]=[C:5]([N+:15]([O-:17])=[O:16])[C:4]([CH:1]4[CH2:2][CH2:3]4)=[CH:11]3)=[N+:12]2[O-:14])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred suspension of compound (iv) (6.2 g, 0.026 mol) in acetic acid (120 mL) was added 4-bromoaniline (9.28 g, 0.054 mol) and the reaction mixture was heated to 60° C. to get a clear solution. To this was added sodium cyanide portionwise (6.2 g, 0.127 mol) and the reaction mixture was stirred at 60° C. for 5 min. Acetic anhydride (1.9 mL, 0.020 mol) was added and the reaction mixture was stirred for 5 min at the same temperature. Sodium cyanide (6.2 g, 0.127 mol) was then added at the same temperature at which time the product precipitated out. The reaction mixture was stirred for 30 min at this temperature and diluted with water (50 mL), filtered and washed with ethanol to give 2-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carbonitrile 1-oxide (v) (4.1 g, 39%).

Workup

customto get a clear solution
stirringthe reaction mixture was stirred for 5 min at the same temperature
customprecipitated out
stirringThe reaction mixture was stirred for 30 min at this temperature
additiondiluted with water (50 mL)
filtrationfiltered
washwashed with ethanol

Sources & evidence

ORD record: ord-9bf2cac820de437199771df1640d3cc8
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546389B2

Reaction notes

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