Sodium Carbonate → 2-Phenylisonicotinic acid

HRID 2387407Notes

Reaction equation

HRID 2387407 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].C([O-])([O-])=O.[Na+].[Na+].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:17]1([C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=2)[C:5]([OH:7])=[O:6])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 2227012-Bromoisonicotinic acid

Product 1

HCID 27628452-Phenylisonicotinic acidYield 60.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

2-Bromoisonicotinic acid (2.02 g, 10 mmol) was dissolved in DMF (80 mL) under argon. Pd(PPh3)4 (0.6 g, 0.52 mmol) was added, and the reaction mixture was stirred at room temperature for 15 min. Na2CO3 (aq. 2N, 40 mL) was then added, followed by the addition of phenylboronic acid (1.67 g, 13.7 mmol). The reaction mixture was heated at 95° C. (18 h), cooled to room temperature and filtered through a celite pad. Water (80 mL) was added, and the mixture was acidified with HCl (2 N) to pH=4. The precipitate was collected via filtration and rinsed with water (2×7 mL). The crude product was recrystallized from 2-methoxylethanol to give 2-phenylisonicotinic acid as a grey solid (1.2 g). 1HNMR (DMSO-d6, 400 MHz): δ 7.51 (m, 3H), 7.78 (d, J=4.8 Hz, 1H), 8.13 (t, J=1.6 Hz, 2H), 8.29 (s, 1H), 8.85 (d, J=4.8 Hz, 1H), 13.73 (bs, 1H).

Workup

  1. temperatureThe reaction mixture was heated at 95° C. (18 h)
  2. temperaturecooled to room temperature
  3. filtrationfiltered through a celite pad
  4. additionWater (80 mL) was added
  5. filtrationThe precipitate was collected via filtration
  6. washrinsed with water (2×7 mL)
  7. customThe crude product was recrystallized from 2-methoxylethanol

Sources & evidence

ORD record
ord-17cd72eb00a1496bbcaa7c3b75c6837e
Source dataset
uspto-grants-2012_09
Patent number
US08268862B2

Reaction notes

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