HCID 10108002, compound → HCID 11777139, compound

HRID 2256495Notes

Reaction equation

HRID 2256495 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:19]([O-])=O)[CH:5]=[C:6]([CH3:18])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH3:17])[CH3:16])[CH:10]=1>[Pt].C(O)C>[CH3:18][C:6]1[CH:5]=[C:4]([CH:3]=[C:2]([CH3:1])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH3:16])[CH3:17])[CH:10]=1)[NH2:19]

Participants

4

Reactant 1

HCID 10108002HCID 10108002, compound

Product 1

HCID 11777139HCID 11777139, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

3,5-Dimethyl-4-(3'-isopropylphenoxy)-nitrobenzene (5.21 g) and 521 mg of 10% platinum on carbon in 150 ml ethanol are reduced under hydrogen on a Parr shaker. The solution is filtered through Celite to remove catalyst and the filtrate is stripped to give 3,5-dimethyl-4-(3'-isopropylphenoxy)-aniline which is then fused with 50 g of dimethyl oxalate at 120° for four hours. The resulting mixture is concentrated under high vacuum and the residue chromatographed on silica gel with 9:1 toluene:ethyl acetate as eluent to yield methyl N-[3,5-dimethyl-4-(3'-isopropylphenoxy)-phenyl]oxarnate; NMR (CDCl3): δ 5 1.2 (6H, d), 2.1 (6H,s), 2.8 (1H,m), 4.0 (3H,s), 6.5 (1H, d of d), 6.7 (1H,t), 6.9 (1H, d of d), 7.2 (1H, t), 7.4 (2H,s), 8.8 (1 h, br s).

Workup

  1. filtrationThe solution is filtered through Celite
  2. customto remove catalyst

Sources & evidence

ORD record
ord-45c2c77287a743d89a5279f9226873ec
Source dataset
uspto-grants-1997_08
Patent number
US05654468

Reaction notes

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