Bicarbonate Ion → 6-(1H-benzimidazol-2-yl)-4-(4-pyridinyl)quinoline

HRID 472079Notes

Reaction equation

HRID 472079 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1N.C(=O)(O)[O-]>>[NH:18]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[C:17]1[C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 769Bicarbonate IonHCID 7243O-PhenylenediamineHCID 667820474-(4-Pyridinyl)-6-quinolinecarbonitrile

Product 1

HCID 598602356-(1H-benzimidazol-2-yl)-4-(4-pyridinyl)quinoline

Conditions

Temperature
250 °C

Procedure

A mixture of 4-(4-pyridinyl)-6-quinolinecarbonitrile, (231 mg, 1 mmol) 1,2-diaminobenzene (108 mg, 1 mmol) and polyphosphoric acid (1.4 g) was heated in the microwave at 250° C. for 1.5 hours. The reaction was poured onto water which was neutralized with bicarbonate. The product was filtered, washed with water, and dried. The product was further purified by dissolving in hot methanol, filtering and cooling to obtain crystals. The yield was 47.7 mg, 30%. MS (ES)+ m/e 323 [M+H]+.

Workup

  1. additionThe reaction was poured onto water which
  2. filtrationThe product was filtered
  3. washwashed with water
  4. customdried
  5. customThe product was further purified
  6. dissolutionby dissolving in hot methanol
  7. filtrationfiltering
  8. temperaturecooling
  9. customto obtain crystals

Sources & evidence

ORD record
ord-806d02af944f4c1fb353cc90b6c6cd1e
Source dataset
uspto-grants-2014_01
Patent number
US08633187B2

Reaction notes

Loading…