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Hydrochloric Acid → 7-Chloro-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid

HRID 1755943
Notes
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Reaction equation

HRID 1755943 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([NH:25][CH:26]3[CH2:31][CH2:30][N:29]([CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:28][CH2:27]3)=[O:24])=[CH:19][CH:18]=1)=[CH:13][CH:12]=[C:11]([Cl:39])[CH:10]=2)=[O:5])C.[OH-].[Na+].Cl>CO>[Cl:39][C:11]1[CH:10]=[C:9]2[C:14]([C:15]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]([NH:25][CH:26]4[CH2:27][CH2:28][N:29]([CH2:32][C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=5)[CH2:30][CH2:31]4)=[O:24])=[CH:21][CH:22]=3)=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)=[CH:13][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 152897657-Chloro-4-[[4-[[[1-(phenylmethyl)-4piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid ethyl ester

Product 1

HCID 152897637-Chloro-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acidYield 64%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

7-Chloro-4-[[4-[[[1-(phenylmethyl)-4piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid ethyl ester (51.7 g, 95.2 mmol) was stirred in 550 ml of methanol and treated with 133 ml of 2.5 M NaOH. The reaction mixture was then refluxed for 45 m at which point the hot homogeneous solution was treated with 166 ml of 2 M HCl to precipitate the product. After the mixture cooled to room temperature, the product was filtered and washed with water, methanol and then ether. The yellow powdery material was then dried in vacuo overnight affording 31.3 g (60.9 mmol, 64% yield) of 7-chloro-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid.

Workup

  1. temperatureThe reaction mixture was then refluxed for 45 m at which point the hot homogeneous solution
  2. customto precipitate the product
  3. filtrationthe product was filtered
  4. washwashed with water, methanol
  5. customThe yellow powdery material was then dried in vacuo overnight

Sources & evidence

ORD record
ord-047bc975c67d4e79a9331ccde7b92feb
Source dataset
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05438064

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes