Ammonia → 8-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 2194936Notes

Reaction equation

[C:1](O)([CH3:4])(C)C.[NH3:6].[Na].C([O:11][CH2:12][CH3:13])(=O)C.[CH3:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>C1COCC1.O>[NH2:6][C:16]1[CH:15]=[CH:14][CH:19]=[C:18]2[C:17]=1[CH2:13][CH:12]([OH:11])[CH2:4][CH2:1]2

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of step-c product (23 g, 0.08 mol) in THF (253 ml, 11 times), tert-butanol (5.93 g (7.54 ml), 0.08 mol, 2.9 eq) was added. Condensed ammonia solution (3.9 ltrs, 170 times) was added (Condensed with the help of ammonia cylinder at −78° C. for 2 hrs). Sodium metal (5.51 g, 0.23 mol, 2.99 eq) was added portion wise (Reaction mixture colour changed during the addition sodium White-Blue—Disappearance of color) at −78° C. The overall reaction mass was stirred for 1.5 hrs at −78° C. and allowed to stir at RT for overnight. Progress of the reaction was monitored by TLC (20% ethyl acetate/hexane, Rf˜0.6). On completion of the reaction, (Total ammonia disappeared), reaction contents were diluted with water (100 ml) and the extracted with ethyl acetate (2×100 ml). Combined extract was dried over sodium sulfate, concentrated under reduced pressure and the crude obtained was purified by column chromatography (silica gel, 8% ethyl acetate/hexane) to yield the required product as a white solid (12 g, 53% yield).

Workup

additionwas added (
customReaction mixture colour
stirringto stir at RT for overnight
extractionthe extracted with ethyl acetate (2×100 ml)
extractionCombined extract
dry with materialwas dried over sodium sulfate
concentrationconcentrated under reduced pressure
customthe crude obtained
customwas purified by column chromatography (silica gel, 8% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-f076ae641fee4f91be8205376e8868f0
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334315B2

Reaction notes

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