Phenol → 4-(Aminocarbonyl)-2-methyl-5-{[2-(methyloxy)ethyl]oxy}benzoic acid

HRID 906159Notes

Reaction equation

HRID 906159 reaction equation
C(C1C(I)=C[C:6]([C:7]([O:9][CH3:10])=O)=C(C)C=1)#N.[C:15]([C:17]1[C:26]([OH:27])=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[C:19]([CH3:28])[CH:18]=1)#[N:16].C1([OH:35])C=CC=CC=1.COCCBr>>[NH2:16][C:15]([C:17]1[C:26]([O:27][CH2:6][CH2:7][O:9][CH3:10])=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[C:19]([CH3:28])[CH:18]=1)=[O:35]

Participants

5

Reactant 4

HCID 996PhenolHCID 809722-Bromoethyl methyl etherHCID 67402433Methyl 4-cyano-5-iodo-2-methylbenzoateHCID 67404603Methyl 4-cyano-5-hydroxy-2-methylbenzoate

Product 1

HCID 577486424-(Aminocarbonyl)-2-methyl-5-{[2-(methyloxy)ethyl]oxy}benzoic acid

Procedure

Synthesized according to the method of reagent preparation 41 by replacement of step 6 with the conversion of methyl 4-cyano-5-iodo-2-methylbenzoate to methyl 4-cyano-5-hydroxy-2-methylbenzoate according to the method described in Chemical & Pharmaceutical Bulletin (2007), 55(9), 1361-1364 followed by phenol alkylation with 2-bromoethyl methyl ether then proceeding with steps 7 and 8. MS (EI) for C12H15NO5: 254 (MH+).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-59b355b37d4b49a4ababb0d816184777
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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