Insnnvnwdycobu-uhfffaoysa- → 7-Hydroxy-5,6,8,9,10,11-hexahydro-4H-dibenzo[de,h]-quinoline

HRID 65694Notes

Reaction equation

[N:1]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[C:7](=[O:15])[C:6]3=[CH:16][CH:17]=[CH:18][C:4]([C:5]=23)=[CH:3][CH:2]=1>C(O)(=O)C.[Pt]>[OH:15][C:7]1[C:8]2[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=2[C:10]2[N:1]=[CH:2][CH:3]=[C:4]3[CH2:18][CH2:17][CH2:16][C:6]=1[C:5]=23

Participants

Conditions

Temperature: 65 °C

Procedure

7H-Dibenzo[de,h]quinol-7-one (48.4 g) and Adams platinum (16 g) suspended in acetic acid (800 cc) are placed under an initial hydrogen pressure of 30 bars at 25° C. The mixture is stirred and heated at 65° C. for 17 hours. After cooling to about 25° C., the catalyst is filtered off and washed twice with acetic acid (total 150 cc). The combined organic filtrates are evaporated to dryness. The residue is taken up in water (1000 cc) and adjusted to pH 9 by the addition of 5N sodium hydroxide. The resulting precipitate is filtered off, washed twice with distilled water (total 2000 cc) and four times with ethanol (total 100 cc) and then dried under reduced pressure (20 mm Hg) at 20° C. Crude 7-hydroxy-5,6,8,9,10,11-hexahydro-4H-dibenzo[de,h]quinoline (46.1 g), melting at 224° C., is thus obtained, which is recrystallised successively from butyl acetate and from propanol as described in Example 3.

Workup

customat 25° C
temperatureAfter cooling to about 25° C.
filtrationthe catalyst is filtered off
washwashed twice with acetic acid (total 150 cc)
customThe combined organic filtrates are evaporated to dryness
additionadjusted to pH 9 by the addition of 5N sodium hydroxide
filtrationThe resulting precipitate is filtered off
washwashed twice with distilled water (total 2000 cc) and four times with ethanol (total 100 cc)
customdried under reduced pressure (20 mm Hg) at 20° C

Sources & evidence

ORD record: ord-9246da8ab0bf4c938585483a5caac7a0
Source dataset: uspto-grants-1978_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04128650

Reaction notes

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