Sodium Hydroxide → HCID 86595225, compound

HRID 2053719Notes

Reaction equation

HRID 2053719 reaction equation
[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH2:5][CH2:4][CH:3]1[OH:15].[OH-].[Na+].[C:18]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:22][C:21]([C:24](Cl)=[O:25])=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.O>[OH:15][CH:3]1[CH2:4][CH2:5][C:6]2[C:11](=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)[CH:2]1[NH:1][C:24]([C:21]1[CH:22]=[CH:23][C:18]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:19][CH:20]=1)=[O:25]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 841514-Phenylbenzoyl chlorideHCID 18463162HCID 18463162, compound

Product 1

HCID 86595225HCID 86595225, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Stir a mixture of 1-amino-7-nitro-1,2,3,4-tetrahydronaphthalen-2-ol (500 mg, 2.40 mmol) and 1N NaOH (4.8 mL, 4.8 mmol) in a mixture of 50 mL of toluene and 50 mL of water for 30 minutes. Added biphenyl-4-carbonyl chloride (570 mg, 2.64 mmol) slowly and stir for four hours at room temperature. Remove the solid by filtration, and wash with toluene. Evaporate solvent under reduced pressure. Biphenyl-4-carboxylic acid (2-hydroxy-7-nitro-1,2,3,4-tetrahydro-naphthalen-1-yl)-amide is obtained in 54% as a white solid: 1H NMR (DMSO-d6) δ 8.87 (1H, d, J=8.4 Hz), 8.03 (2H, d, J=8.4 Hz), 7.99 (2H, d, J=7.6 Hz), 7.79 (2H, d, J=8.4 Hz), 7.74 (2H, d, J=8.4 Hz), 7.50 (2H, t, J=7.2 Hz), 7.43(2H, t, J=6.8 Hz), 5.22 (1H, d, J=4.4 Hz), 5.11 (1H, t, J=7.6 Hz), 3.95-4.01 (1H, m), 2.87-3,07(2H, m), 2.08-2.15 (1H, m), 1.81-1.94 (1H, m); MS 389(MH+). The above compound (0.25 g, 0.64 mmol) is reduced in 10 mL of DMF with 48 mg of 10% Pd-C at room temperature under 60 psi (414 kPa) for overnight to form biphenyl-4-carboxylic acid (7-amino-2-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-amide, obtained in 96% as a yellow oil. MS 359 (MH+).

Workup

  1. customRemove the solid
  2. filtrationby filtration
  3. washwash with toluene

Sources & evidence

ORD record
ord-7c87402f70f94a91a0830a48af5b2222
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

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