Hydrochloric Acid → 4-Amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid

HRID 2197519Notes

Reaction equation

[NH2:1][C:2]1[C:7]2=[C:8]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[C:9]([C:11]([O:13]CC)=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[OH-].[Na+].Cl>C(O)C.C1COCC1>[NH2:1][C:2]1[C:7]2=[C:8]([C:16]3[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=3)[C:9]([C:11]([OH:13])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of ethyl 4-amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (1.04 g, 3.18 mmol) in ethanol (10 mL), THF (5 mL) and 1N aqueous sodium hydroxide solution (5.56 mL, 5.56 mmol) was heated (80° C.) for 6 h. The homogeneous solution was cooled to rt and treated dropwise with 1N hydrochoric acid (5.56 mL). The reaction was concentrated in vacuo and the resulting solid triturated with water to give the desired product in quantitative yield. This material could be used without further purification. ES-MS 300.2 (MH)+; HPLC RT (Method A) 1.37 min.

Workup

temperatureThe homogeneous solution was cooled to rt
concentrationThe reaction was concentrated in vacuo
customthe resulting solid triturated with water

Sources & evidence

ORD record: ord-eb4408e076ff470ba82ccfd12655de0d
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338594B2

Reaction notes

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