Ethyl 7-(2-chloroethoxy)-6-methoxy-3-nitro-2-naphthoate → Ethyl 3-amino-7-(2-chloroethoxy)-6-methoxy-2-naphthoate

HRID 989355Notes

Reaction equation

HRID 989355 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([N+:20]([O-])=O)[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12]2)=[CH:7][C:6]=1[O:23][CH3:24].[Cl:25][CH2:26][CH2:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[CH:35]=[C:34]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:33]([N+:46]([O-])=O)=[CH:32]2>C(O)C.[Pd]>[NH2:20][C:10]1[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][C:13]2[C:8]([CH:9]=1)=[CH:7][C:6]([O:23][CH3:24])=[C:5]([O:4][CH2:3][CH2:2][Cl:1])[CH:14]=2.[NH2:46][C:33]1[C:34]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[CH:35][C:36]2[C:31]([CH:32]=1)=[CH:30][C:29]([O:28][CH2:27][CH2:26][Cl:25])=[C:38]([O:39][CH3:40])[CH:37]=2

Participants

6

Reactant 2

HCID 9968466Ethyl 7-(2-chloroethoxy)-6-methoxy-3-nitro-2-naphthoateHCID 9968467Ethyl 6-(2-chloroethoxy)-7-methoxy-3-nitro-2-naphthoate

Product 2

HCID 9858408Ethyl 3-amino-7-(2-chloroethoxy)-6-methoxy-2-naphthoateHCID 11594979Ethyl 3-amino-6-(2-chloroethoxy)-7-methoxy-2-naphthoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 1.60 g portion of ethyl 7-(2-chloroethoxy)-6-methoxy-3-nitro-2-naphthoate and ethyl 6-(2-chloroethoxy)-7-methoxy-3-nitro-2-naphthoate (1:1 mixture) is heated in 100 mL absolute ethanol until dissolved. The solution is allowed to cool to room temperature and 0.2 g of 10% palladium on carbon is added. Hydrogenation is carried out in a Parr apparatus at 50 psi for 2 hours. The reaction mixture is filtered through celite and the filter cake is rinsed with ethanol. The filtrate and washes are combined and evaporated to give ethyl 3-amino-7-(2-chloroethoxy)-6-methoxy-2-naphthoate and ethyl 3-amino-6-(2-chloroethoxy)-7-methoxy-2-naphthoate (1:1 mixture) as a greenish yellow solid, 1.28 g (87%), m.p. 104-8° C.

Workup

  1. dissolutionuntil dissolved
  2. filtrationThe reaction mixture is filtered through celite
  3. washthe filter cake is rinsed with ethanol
  4. customevaporated

Sources & evidence

ORD record
ord-2da029d47fa646819794f7bd1639956f
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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