Phenol → 4-(Aminocarbonyl)-2-methyl-5-(methyloxy)benzoic acid

HRID 906157Notes

Reaction equation

HRID 906157 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(C1C(O)=CC([C:21](OC)=[O:22])=C(C)C=1)#N.C1([OH:35])C=CC=CC=1.IC>>[NH2:2][C:1]([C:3]1[C:12]([O:22][CH3:21])=[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 6328Methyl iodideHCID 67402433Methyl 4-cyano-5-iodo-2-methylbenzoateHCID 67404603Methyl 4-cyano-5-hydroxy-2-methylbenzoate

Product 1

HCID 577483284-(Aminocarbonyl)-2-methyl-5-(methyloxy)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 iodomethane then proceeding with steps 7 and 8. 1H NMR (400 MHz, DMSO-d6): 7.69 (b, 1H), 7.63 (b, 2H), 7.45 (s, 1H), 3.88 (s, 3H), 2.44 (s, 3H); MS (EI) for C10H11NO4: 210 (MH+).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-392191fc0e6849f796f9785962831b31
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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