Sodium Hydroxide → 6-[(3,3,3-Trifluoropropyl)carbamoyl]nicotinic acid

HRID 1099438Notes

Reaction equation

HRID 1099438 reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][N:9]=1)=[O:7].[OH-].[Na+]>C(O)C>[F:19][C:2]([F:1])([F:18])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][N:9]=1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59354919HCID 59354919, compound

Product 1

HCID 593549216-[(3,3,3-Trifluoropropyl)carbamoyl]nicotinic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 6-[(3,3,3-trifluoropropyl)carbamoyl]nicotinate (0.265 g, 0.96 mmol), sodium hydroxide (9.60 ml, 9.60 mmol), and ethanol (10 mL) was heated to 50° C. for 3.5 h. The volatiles were removed in vacuo. The residue was suspended in water (20 mL) and insoluble material was filtered off. The filtrate was cooled on ice and 6 M hydrochloric acid was added while stirring until an acidic pH was reached. The precipitate was filtered off, washed with ice-water and dried in vacuo to yield 78 mg (31%); MS (APPI/APCI) m/z 263[M+H+].

Workup

  1. customThe volatiles were removed in vacuo
  2. filtrationinsoluble material was filtered off
  3. temperatureThe filtrate was cooled on ice and 6 M hydrochloric acid
  4. additionwas added
  5. filtrationThe precipitate was filtered off
  6. washwashed with ice-water
  7. customdried in vacuo
  8. customto yield 78 mg (31%)

Sources & evidence

ORD record
ord-bc59ad27459948d6863da341f74c1159
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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