Hydroxyamine hydrochloride → HCID 68692740, compound

HRID 1928384Notes

Reaction equation

HRID 1928384 reaction equation
CC1[N:3]([C:8]2[CH:13]=[C:12]([C:14]3[N:19]=[C:18]([C:20]4[CH:25]=[C:24]([C:26]5[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=5)[CH:23]=[C:22]([CH3:36])[N:21]=4)[CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:10][N:9]=2)C(C)=CC=1.Cl.NO>>[CH3:36][C:22]1[N:21]=[C:20]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([C:12]3[CH:11]=[CH:10][N:9]=[C:8]([NH2:3])[CH:13]=3)[N:19]=2)[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:28][CH:27]=2)[CH:23]=1

Participants

3

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 68691006HCID 68691006, compound

Product 1

HCID 68692740HCID 68692740, compoundYield 27.9%

Procedure

A mixture of the above described 2″-(2,5-dimethyl-pyrrol-1-yl)-6-methyl-4-(4-trifluoromethyl-phenyl)-[2,2′;6′,4″]terpyridine (470 mg, 0.969 mmol), hydroxylamine hydrochloride (337 mg, 4.849 mmol) 1.5 M NaOH-sol. (1.62 mL, 2.43 mmol) in 1-propanole (5 mL) was stirred at 120° C. for 3 h in a sealed tube. Cooled to rt, poured the reaction mixture directly on a silica gel column and chromatographed with EtOAc followed by trituration with diethyl ether/heptane to give the title compound (0.110 g, 27%) as a light yellow solid. MS (ISP) 407.3 [(M+H)+]; mp 160° C.

Workup

  1. additionA mixture of the
  2. additionpoured the reaction mixture directly on a silica gel column
  3. customchromatographed with EtOAc

Sources & evidence

ORD record
ord-4c71e085c7f34d02b420b7f6743fffe5
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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