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Sulfuric Acid → 4-[4-(3-Chloro-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-yloxy]-cyclohexanone

HRID 386595
Notes
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Reaction equation

HRID 386595 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[C:8]([F:37])=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:35][CH3:36])=[C:21]([O:24][CH:25]4[CH2:34][CH2:33][C:28]5(OCC[O:29]5)[CH2:27][CH2:26]4)[CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1.[OH-].[Na+]>O1CCCC1>[Cl:6][C:7]1[C:8]([F:37])=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:35][CH3:36])=[C:21]([O:24][CH:25]4[CH2:34][CH2:33][C:28](=[O:29])[CH2:27][CH2:26]4)[CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 591581734-[(3-Chloro-2-fluoro-phenyl)amino]-6-(1,4-dioxa-spiro[4.5]decan-8-yl-oxy)-7-methoxy-quinazoline

Product 1

HCID 581572644-[4-(3-Chloro-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-yloxy]-cyclohexanone

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Procedure

25 ml of 4M sulphuric acid are added to 9.0 g 4-[(3-chloro-2-fluoro-phenyl)amino]-6-(1,4-dioxa-spiro[4.5]decan-8-yl-oxy)-7-methoxy-quinazoline in 110 ml of tetrahydrofuran and the mixture is stirred for 18 hours at ambient temperature. The mixture is made alkaline with 4M sodium hydroxide solution and extracted several times with ethyl acetate. The combined organic phases are dried, evaporated down and stirred with diethyl ether. The solid is suction filtered and dried.

Workup

  1. extractionextracted several times with ethyl acetate
  2. customThe combined organic phases are dried
  3. customevaporated down
  4. stirringstirred with diethyl ether
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-90d2a74060284b13b9cf32541f09e6c0
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08372855B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes