Ammonium Hydroxide → 7-Methoxynaphthalen-2-amine

HRID 1772269Notes

Reaction equation

HRID 1772269 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](O)=[CH:10]2)=[CH:5][CH:4]=1.OS([O-])=O.[Na+].[OH-].[NH4+:20]>>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([NH2:20])=[CH:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 8531737-Methoxy-2-naphtholHCID 23665763Sodium Bisulfite

Product 1

HCID 148760287-Methoxynaphthalen-2-amineYield 70%

Procedure

The solution of 7-methoxynaphthalen-2-ol (6.5 g, 37.31 mmol) and NaHSO3 (11.6 g, 111.54 mmol) in ammonium hydroxide (100 ml) was stirred for 2 days at 140° C. in a sealed tube and then cooled to room temperature. The solids were collected by filtration to afford 7-methoxynaphthalen-2-amine as an off-white solid (4.5 g, 70%). (ES, m/z): [M+H]+ 174.1; 1H NMR (300 MHz, CDCl3): δ 7.57 (d, J=8.7 Hz, 2H), 6.97-6.87 (m, 3H), 6.79 (dd, J=8.7, 2.1 Hz, 1H), 3.90 (s, 3H), 3.84 (br s, 2H).

Workup

  1. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-08cdab5cddce402e961f33a26ba3cdee
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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