Hydrochloric Acid → {9-[(3-Methylphenyl)methyl]-2-methyl-5-carbamoylcarbazol-4-yl}oxyacetic acid

HRID 51331Notes

Reaction equation

HRID 51331 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:21]3[CH:20]=[C:19]([CH3:22])[CH:18]=[C:17]([O:23][CH2:24][C:25]([O:27]C)=[O:26])[C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][C:14]=3[C:29](=[O:31])[NH2:30])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:21]3[CH:20]=[C:19]([CH3:22])[CH:18]=[C:17]([O:23][CH2:24][C:25]([OH:27])=[O:26])[C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][C:14]=3[C:29](=[O:31])[NH2:30])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86756258{9-[(3-Methylphenyl)methyl)-2-methyl-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl ester

Product 1

HCID 9930948{9-[(3-Methylphenyl)methyl]-2-methyl-5-carbamoylcarbazol-4-yl}oxyacetic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of {9-[(3-methylphenyl)methyl)-2-methyl-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl ester (0.12 g, 0.288 mM) and 1.4 mL (2.8 mM) of 2 N NaOH in 14 mL of ethanol was stirred for 30 minutes at 25° C. The reaction was acidified with 1N HCl to pH=2. After stirring 1 hour, the resultant white precipitate was collected by filtration, washed with water, then dried in vacuo to afford 114 mg (95%) {9-[(3-methylphenyl)methyl]-2-methyl-5-carbamoylcarbazol-4-yl}oxyacetic acid. 1H NMR (DMSO-d6) δ11.1 (bs, 1H), 7.75 (bs, 1H), 7.6 (d, J=8 Hz, 1H), 7.45 (bs, 1H), 7.35 (dd, J=8 and 8 Hz, 1H), 7.2-7.0 (m, 5H), 6.85 (d, J=8 Hz, 1H), 6.45 (s, 1H), 5.6 (s, 2H), 4.8 (s, 2H), 2.4 (s, 3H), 2.2 (s, 3H). MS (ES) m/e 386, 403. Recrystallization from acetone/hexane provided an analytical sample:

Workup

  1. filtrationthe resultant white precipitate was collected by filtration
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-657976a4a74d472fbed499600c06233d
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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