N-bromobutanimide → HCID 88142889, compound

HRID 1638708Notes

Reaction equation

HRID 1638708 reaction equation
[C:1]([O:4][C:5]1[N:6]=[C:7]([CH3:22])[C:8]2[C:13]([C:14]=1[N+:15]([O-:17])=[O:16])=[CH:12][C:11]([O:18][CH3:19])=[C:10]([O:20][CH3:21])[CH:9]=2)(=[O:3])[CH3:2].[Br:23]N1C(=O)CCC1=O.C(Cl)Cl.CCCCCC>C(Cl)Cl>[OH2:3].[C:1]([O:4][C:5]1[N:6]=[C:7]([CH2:22][Br:23])[C:8]2[C:13]([C:14]=1[N+:15]([O-:17])=[O:16])=[CH:12][C:11]([O:18][CH3:19])=[C:10]([O:20][CH3:21])[CH:9]=2)(=[O:3])[CH3:2].[C:1]([O:4][C:5]1[N:6]=[C:7]([CH2:22][Br:23])[C:8]2[C:13]([C:14]=1[N+:15]([O-:17])=[O:16])=[CH:12][C:11]([O:18][CH3:19])=[C:10]([O:20][CH3:21])[CH:9]=2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 14626131HCID 14626131, compoundHCID 21226440Methylenechloride Hexane

Product 1

HCID 88142889HCID 88142889, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-acetoxy-6,7-dimethoxy-1-methyl-4-nitroisoquinoline (4.0 g, 13.06 mmol) in methylene chloride (100 mL) and N-bromosuccinimide (2.8 g, 15.66 mmol) was heated to reflux under nitrogen for 17 hours. The mixture was evaporated to dryness. The residue was redissolved in methylene chloride (60 mL) and the major product was isolated by chromatography on a silica gel column (low pressure) using 7:3 methylene chloride/hexane as the eluent to yield the title compound (2.13 g, 39%). One recrystallization from methylene chloride/ether gave the purified title compound as a lemon yellow crystalline solid (2.08 g, 38.7%), mp 194°-195° C. (d). IR (KBr) 1777, 1174 cm-1 ; NMR (CDCl3): δ 2.40 (s, 3H, OCOCH3), 4.05 (s, 3H, OCH3), 4.10 (s, 3H, OCH3), 4.90 (s, 2H, 1-CH2Br), 7.30 (s, 1 H, B 5- or 8-H), 7.43 (s, 1H, 5- or 8-H); MS (DCI): 385 (MH)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 17 hours
  3. customThe mixture was evaporated to dryness
  4. dissolutionThe residue was redissolved in methylene chloride (60 mL)
  5. customthe major product was isolated by chromatography on a silica gel column (low pressure)

Sources & evidence

ORD record
ord-ba14f83e186b409b928d2b8f827e1bac
Source dataset
uspto-grants-1989_11
Patent number
US04880817

Reaction notes

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