Phenol → 4-(Aminocarbonyl)-2-methyl-5-[(1-methylpropyl)oxy]benzoic acid

HRID 906158Notes

Reaction equation

HRID 906158 reaction equation
[C:1]([C:3]1[C:12](I)=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[C:5]([CH3:14])[CH:4]=1)#[N:2].C([C:17]1[C:26]([OH:27])=[CH:25][C:20](C(OC)=O)=C(C)C=1)#N.C1([OH:35])C=CC=CC=1.BrC(CC)C>>[NH2:2][C:1]([C:3]1[C:12]([O:27][CH:26]([CH3:17])[CH2:25][CH3:20])=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:14])[CH:4]=1)=[O:35]

Participants

5

Reactant 4

HCID 996PhenolHCID 65542-BromobutaneHCID 67402433Methyl 4-cyano-5-iodo-2-methylbenzoateHCID 67404603Methyl 4-cyano-5-hydroxy-2-methylbenzoate

Product 1

HCID 577483964-(Aminocarbonyl)-2-methyl-5-[(1-methylpropyl)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-bromobutane then proceeding with steps 7 and 8. MS (EI) for C13H17NO4: 252 (MH+).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-27addd7e206443028efc53bbaa1e3cc7
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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