1,4-Dibromo-2-nitrobenzene → HCID 62896872, compound

HRID 1817893Notes

Reaction equation

HRID 1817893 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Cl.[NH2:13][CH2:14][C:15]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)C(C)C)(C)C>CN1CCCC1=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:13][CH2:14][C:15]2([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 770041,4-Dibromo-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 211096931-(Aminomethyl)cyclopentan-1-ol--hydrogen chloride (1/1)

Product 1

HCID 62896872HCID 62896872, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The mixture of 2,5-dibromonitrobenzene (Tokyo Kasei Kogyo Co., Ltd., 5.4 g, 19.2 mmol), 1-(aminomethyl)cyclopentanol hydrochloride (J. Med. Chem. 1981, 24, 12-16, 4.3 g, 28.4 mmol) and N,N-diisopropylethylamine (8.4 mL, 48.1 mmol) in 1-methyl-2-pyrrolidinone (32 mL) was microwaved for 30 min at 200° C. The reaction was quenched with water and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 as eluent) to afford the title compound (2.6 g, 43%) as an orange amorphous solid.

Workup

  1. customwas microwaved for 30 min at 200° C
  2. customThe reaction was quenched with water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 as eluent)

Sources & evidence

ORD record
ord-42a2a21addcc496abd29a1388410969d
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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