HCID 22504197, compound → HCID 22504019, compound

HRID 1814309Notes

Reaction equation

HRID 1814309 reaction equation
[C:1]1([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=2[N+:23]([O-])=O)[C:17]([NH2:19])=[O:18])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H][H]>O1CCCC1.[Ni]>[NH2:23][C:22]1[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][C:14]=1[O:13][CH2:12][CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 22504197HCID 22504197, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22504019HCID 22504019, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-naphthalen-1-yl-ethoxy)-4-nitro-benzamide (0.500 g, 1.48 mmol) in 75 mL of tetrahydrofuran at room temperature was added Raney Nickel (0.50 g). The reaction was pressurized to 50 psi of hydrogen for 18 hours. The reaction was then filtered through celite and washed with tetrahydrofuran. The filtrate was then concentrated in vacuo to dryness to yield 4-amino-3-(2-naphthalen-1-yl-ethoxy)-benzamide 455 mg (100%) of a white solid. 1HNMR(300 MHz, DMSO) 8.26 (d, 1H), 7.99 (d, 1H), 7.98 (d,1H), 7.68(m, 5H), 7.33 (m, 2H), 6.93 (bs, 1H), 6.62 (d, 1H), 4.89 (s, 2H), 5.16 (s, 2H), 4.34 (t, 2H), 3.63 (t, 2H). MS(APCI) m/z 307.1 (M+H).

Workup

  1. filtrationThe reaction was then filtered through celite
  2. washwashed with tetrahydrofuran
  3. concentrationThe filtrate was then concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-56b231a3a80945189f2f78735e4e5e4d
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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