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Dimethylformamide → 4-(4-Aminocarbonylphenoxy)butanoic acid ethyl ester

HRID 345111
Notes
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Reaction equation

HRID 345111 reaction equation
[CH:1]1[C:6](CC(N)=O)=[CH:5][CH:4]=[C:3]([OH:11])[CH:2]=1.Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])([O-])=O.[K+].[K+].C[N:28]([CH:30]=[O:31])C>O>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][CH2:14][CH2:13][O:11][C:3]1[CH:4]=[CH:5][C:6]([C:30]([NH2:28])=[O:31])=[CH:1][CH:2]=1)[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 86986(4-Hydroxyphenyl)acetamide

Product 1

HCID 536789844-(4-Aminocarbonylphenoxy)butanoic acid ethyl esterYield 60%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixture of p-hydroxyphenylacetamide (3.8 g), ethyl 4-bromobutyrate (3.6 ml) and K2CO3 (3.45 g) was stirred for 12 hr in DMF (30 ml). The mixture was diluted with water (100 ml); the solid was filtered and air dried. Crystallization of the solid from ethanol gave 4 g (60%) of the title compound as white crystals; mp 144.5°-145.5°.

Workup

  1. filtrationthe solid was filtered
  2. customair dried
  3. customCrystallization of the solid from ethanol

Sources & evidence

ORD record
ord-c1184a658fdf48baa9363524f504f96a
Source dataset
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05055450

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes