Sodium Hydroxide → HCID 67057785, compound

HRID 1058321Notes

Reaction equation

HRID 1058321 reaction equation
[C:1]1([C:7]2[C:12]([C:13](O)=O)=[CH:11][N:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:16].[Na+]>>[C:11]1(=[O:16])[C:12]2[C:7]([C:1]3[C:6]([CH:13]=2)=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][CH:9]=[N:10]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 27629334-PHENYLNICOTINIC ACID

Product 1

HCID 67057785HCID 67057785, compound

Conditions

Temperature
200 °C

Procedure

4-Phenylnicotinic acid (4.7 g, 23.8 mmol) from the previous step was suspended in polyphosphoric acid (160.3 g) and slowly heated to 200° C. with stirring. After 5 hours, the mixture was cooled to 140° C. and slowly poured over crushed ice and stirred for 24 hours. The mixture was then neutralized to pH=4 with 50% sodium hydroxide solution and extracted 3 times with dichloromethane. The dichloromethane extracts were combined and the solvent was removed under reduced pressure to yield the yellow solid of 2-azafluorenone (3.1 g, HPLC RT=2.16 min, method A; LC-MS m/z=182), 1H NMR, 400 MHz, CHCl3, 8.72 ppm (s, 1H), 8.75 ppm (d, 1H), 7.75 ppm (d, 1H), 7.65 ppm (d, 1H), 7.62-7.55 ppm (m, 1H), 7.51-7.46 ppm (m, 2H).

Workup

  1. temperaturethe mixture was cooled to 140° C.
  2. additionslowly poured
  3. customover crushed ice
  4. stirringstirred for 24 hours
  5. extractionextracted 3 times with dichloromethane
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-430d072d8df24ae0a1ef1da777fe9141
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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