3,5-Dichloro-4-ethoxybenzoic acid → Methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-chlorobenzoate

HRID 62722

Reaction equation

HRID 62722 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:14])[C:10]=1[O:11][CH2:12][CH3:13])[C:5]([OH:7])=O.[NH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([Cl:26])[CH:17]=1>>[Cl:14][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([Cl:1])[C:10]=1[O:11][CH2:12][CH3:13])[C:5]([NH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([Cl:26])[CH:17]=1)=[O:7]

Participants

3

Reactant 2

HCID 8201383,5-Dichloro-4-ethoxybenzoic acidHCID 11839197Methyl 4-Amino-2-chlorobenzoate

Product 1

HCID 67041552Methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-chlorobenzoateYield 39%

Procedure

Methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-chlorobenzoate (AAA-017) (175 mg, 39%) was prepared in essentially the same manner as in Step (iii) for AAA-001, except that 3,5-dichloro-4-ethoxybenzoic acid was used instead of 3,5-dichloro-4-(cyclopentyloxy)benzoic acid and methyl 4-amino-2-chlorobenzoate was used instead of methyl 4-aminobenzoate: m/z 402 (M−H)− (ES−). 1H NMR (400 MHz, CDCl3) δ: 7.93 (2H, d), 7.85 (1H, s), 7.83 (1H, d), 7.80 (2H, s), 4.18 (2H, q), 3.93 (3H, s), 1.49 (3H, t).

Sources & evidence

ORD record
ord-ce75ea05cf8d45b1bed3f16a3947ac22
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Linked notes

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