Methanol → 1-Acetamido-4-bromo-2-nitro-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene

HRID 863523Notes

Reaction equation

HRID 863523 reaction equation
[C:1]([NH:4][C:5]1[C:14]2[CH2:13][CH:12]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:11][CH2:10][C:9]=2[C:8]([Br:20])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[N+:21]([O-])([OH:23])=[O:22].CCOC(C)=O.CO>FC(F)(F)C(O)=O>[C:1]([NH:4][C:5]1[C:14]2[CH2:13][CH:12]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:11][CH2:10][C:9]=2[C:8]([Br:20])=[CH:7][C:6]=1[N+:21]([O-:23])=[O:22])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 944Nitric AcidHCID 8857Ethyl AcetateHCID 196962081-Acetamido-4-bromo-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene

Product 1

HCID 196962571-Acetamido-4-bromo-2-nitro-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1-acetamido-4-bromo-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene (0.3 g) in trifluoroacetic acid (10 mL) was cooled in an icebath and treated with fuming nitric acid (0.5 mL). After stirring for 4 h, the solvent was evaporated and the residue taken up in methylene chloride:water. The mixture was basified with 12.5% NaOH, and the aqueous layer back extracted. The combined organic layers were dried over sodium sulfate, filtered and evaporated to give a solid. Preparative thin layer chromatography (7:3 EtOAc:MeOH) was used to obtain the purified product (0.12 g).

Workup

  1. temperaturewas cooled in an icebath
  2. customthe solvent was evaporated
  3. extractionthe aqueous layer back extracted
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a solid

Sources & evidence

ORD record
ord-a4b05536447847489ca020887ff9e7f9
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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