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Hydrochloric Acid → 4-(2-Carboxymethoxy-ethylamino)-3-fluoro-benzoic acid

HRID 2222548
Notes
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Reaction equation

HRID 2222548 reaction equation
ClCCO[N:5]([C:18](=O)[CH3:19])[C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][C:7]=1[F:17].[OH-:21].[K+].Cl.ClCCl.[O:27]1[CH2:32][CH2:31][O:30]CC1>O>[C:31]([CH2:32][O:27][CH2:19][CH2:18][NH:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[F:17])([OH:30])=[O:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 86600579Ethyl 4-[(2-chloro-ethoxy)-acetyl-amino]-3-fluoro-benzoate

Product 1

HCID 667315904-(2-Carboxymethoxy-ethylamino)-3-fluoro-benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

580 mg (1.91 mmol) ethyl 4-[(2-chloro-ethoxy)-acetyl-amino]-3-fluoro-benzoate in 6 ml dioxane are combined with 3.82 ml (7.64 mmol) 2-molar potassium hydroxide solution and 2 ml of water. Then the mixture is heated to 70° C. for 2 h, then diluted with water and acidified with 6-molar hydrochloric acid. After the addition of dichloromethane the precipitate formed is suction filtered and dried in the drying cupboard at 50° C.

Workup

  1. customformed
  2. filtrationfiltered
  3. customdried in the drying cupboard at 50° C.

Sources & evidence

ORD record
ord-a7f9abb99a114c9bbc9ffa33aaba3d05
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07371743B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes