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

HRID 871324Notes

Reaction equation

HRID 871324 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([O:19][CH3:20])=[CH:8][C:9]([N+:16]([O-])=O)=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12]>CCOC(C)=O.[Pd]>[NH2:16][C:9]1[CH:8]=[C:7]([O:19][CH3:20])[C:6]([O:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 1

HCID 11666631Methyl 5-(3-chloropropoxy)-4-methoxy-2-nitrobenzoate

Product 1

HCID 23032997Methyl 2-amino-5-(3-chloropropoxy)-4-methoxybenzoateYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In the manner described in Example 16A Step 3, methyl 5-(3-chloropropoxy)-4-methoxy-2-nitrobenzoate (6.70 g, 22.1 mmol) in EtOAc (100 mL) was reacted with 10% palladium on carbon as described in Example 16A Step 3 to give methyl 2-amino-5-(3-chloropropoxy)-4-methoxybenzoate (6.0 g, 22.0 mmol, 99%). 1H NMR (300 MHz, DMSO-d6) δ 7.18 (s, 1H), 6.49 (br s, 2H), 6.37 (s, 1H), 3.93 (t, 2H), 3.82-3.71 (m, 8H), 2.14-2.06 (m, 2H); LC-MS (ESI) m/z 274 (M+H)+.

Sources & evidence

ORD record
ord-ca26be95be4a443d956fcb1b1aadcc2f
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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