Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate → Methyl 2-amino-4-(3-chloropropoxy)-5-methoxybenzoate

HRID 631255Notes

Reaction equation

HRID 631255 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])=[CH:6][C:5]=1[N+:17]([O-])=O>C(OCC)(=O)C.CO.[Pd]>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])=[CH:6][C:5]=1[NH2:17]

Participants

4

Reactant 1

HCID 23032992Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate

Product 1

HCID 23033013Methyl 2-amino-4-(3-chloropropoxy)-5-methoxybenzoateYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of the intermediate from Step 2 (29.14 g, 95.8 mmol) in ethyl acetate: methanol (3:1, 1 L) was added 10% Pd/C (3 g). The mixture was stirred under H2 for 12 hours. Completion of the reaction was monitored by LCMS. The reaction mixture was filtered using a celite pad and washed with excess ethyl acetate. The filtrate was evaporated to dryness to afford the pure 2-amino-4-(3-chloro-propoxy)-5-methoxy-benzoic acid methyl ester (24.2 g, 94%) as a solid. 1H NMR (300 MHz, DMSO-d6) δ 7.13 (s, 1H), 6.43 (s, 2H), 6.39 (s, 1H), 4.04 (t, 2H), 3.80 (t, 2H), 3.74 s, 3H), 3.65 (s, 3H), 2.19 (m, 2H), LC-MS (ESI)m/z 274 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with excess ethyl acetate
  3. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-496c384a2b264d5f9b0dcf9b5f780fd1
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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