Sodium Hydroxide → HCID 20258997, compound

HRID 1004581Notes

Reaction equation

HRID 1004581 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7]([N:11]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)=[CH:6][C:5]=1[NH:18]C(=O)C)([O-:3])=[O:2].[OH-].[Na+]>CO>[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7]([N:11]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)=[CH:6][C:5]=1[NH2:18])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18792763HCID 18792763, compound

Product 1

HCID 20258997HCID 20258997, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[2-Nitro-4-fluoro-5-(4-hydroxypiperidin-1-yl)phenyl]acetamide (10.0 g, 0.034 mol) (obtained in preparation 6, step 1) was deacetylated using 6 N NaOH solution (20 mL) and methanol (30 mL) using an analogous procedure to that described in preparation 4 (step 2) to afford 2-nitro-4-fluoro-5-(4-hydroxypiperidin-1-yl) aniline (8.4 g, 80%). mp 238-239 ° C.; IR (KBr) 3357, 3326, 1641 cm-1 ; 1H NMR (CDCl3) δd 1.70-1.80 (m, 2H, CH2), 1.99-2.08 (m, 2H, CH2), 2.99-3.12 (m, 2H, NCH2), 3.50-3.62 (m, 2H, NCH2), 3.94 (m, 1H, CH), 6.0 (d, J=7.4 Hz, 1H), 6.02 (brs, 2H, NH2), 7.80 (d, J=14.2 Hz, 1H); Mass (m/z) 255 (M+.).

Workup

  1. customthat described in preparation 4 (step 2)

Sources & evidence

ORD record
ord-04eb37119e1e4d3fba77512aea8d60db
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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