HCID 67042219, compound → Methyl 4-amino-3,5-diisopropoxybenzoate

HRID 62749Notes

Reaction equation

HRID 62749 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:18][CH:19]([CH3:21])[CH3:20])[C:14]=1[N+:15]([O-])=O)[C:8]([O:10][CH3:11])=[O:9])([CH3:3])[CH3:2]>CO.C(O)=O.[Pd]>[NH2:15][C:14]1[C:13]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:4][CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 67042219HCID 67042219, compound

Product 1

HCID 67041607Methyl 4-amino-3,5-diisopropoxybenzoateYield 74.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

Methyl 3,5-diisopropoxy-4-nitrobenzoate (3) (594 mg, 2.00 mmol) was dissolved in a mixture of MeOH (40 mL) and formic acid (5 mL) and was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 40° C. under H2 (full H2 mode). The solvents were removed in vacuo to yield methyl 4-amino-3,5-diisopropoxybenzoate (4) (398 mg, 72%) as a pale yellow oil: 1H NMR (400 MHz, CDCl3) δ: 7.20 (2H, s), 4.59 (2H, sep), 4.23 (2H, br s), 3.83 (3H, s), 1.33 (12H, d).

Workup

  1. customat 40° C.
  2. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-91b05a97d1fd4cc3a351dc99a3c1c6c2
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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