2-Chloronicotinic acid → HCID 13776180, compound

HRID 1898880Notes

Reaction equation

HRID 1898880 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([NH2:21])[CH:15]=1)([O-:13])=[O:12]>>[N+:11]([C:14]1[CH:19]=[CH:18][C:17]2[NH:20][C:4](=[O:6])[C:3]3[CH:7]=[CH:8][CH:9]=[N:10][C:2]=3[NH:21][C:16]=2[CH:15]=1)([O-:13])=[O:12]

Participants

3

Reactant 2

HCID 762582-Chloronicotinic acidHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 13776180HCID 13776180, compoundYield 82%

Conditions

Temperature
170 °C

Procedure

A mixture of 2-chloronicotinic acid (15.7 g, 0.1 mol) and 4-nitrophenylene diamine (15.3 g, 0.1 mol) was heated in sulfonane (100 ml) at 170° C. for 5 hrs. The reaction mixture was then cooled and left standing overnight. The solid material was filtered and taken up in boiling ethanol. The solid was filtered again an dried giving 21 g (82% theory) of 6,11-dihydro-9-nitro-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one suitable for use in the next reaction.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. waitleft
  3. filtrationThe solid material was filtered
  4. filtrationThe solid was filtered again an dried

Sources & evidence

ORD record
ord-697b746758e248819b122d69c644bea8
Source dataset
uspto-grants-1996_11
Patent number
US05571809

Reaction notes

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