Imidazole → HCID 18926613, compound

HRID 1600165Notes

Reaction equation

HRID 1600165 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=2)[NH:6][CH:5]=1.[NH:17]1C=CN=[CH:18]1>C1(C)C(C)=CC=CC=1>[N:2]1([CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=3)[NH:6][CH:5]=2)[CH:16]=[CH:18][N:17]=[CH:1]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 18882Indole, 3-((dimethylamino)methyl)-5-nitro-

Product 1

HCID 18926613HCID 18926613, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of N,N-dimethyl-5-nitro-1H-indole-3-methanamine (J.Med, Chem, 9, 140,(1966)) (9.10 g) and imidazole (2.96 g) in xylene (120 ml) was heated under reflux for 2.5 hours and then cooled. The solid was filtered off, washed with ether and dried to give the title compound (9.40 g), m.p. 230°-232° C. (from ethyl acetate/methanol). Found: C,59.85; H,4.39; N,22.80. C12H10N4O2 requires: C,59.50; H,4.16; N,23.13%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. temperaturecooled
  4. filtrationThe solid was filtered off
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-dab7a92d21104d1abe9121c894b2b43a
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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