Isopropylamine → TRANS-4-ISOPROPYLAMINO-3,4-DIHYDRO-2H-NAPHTHO[1,2-b]PYRAN-3-OL

HRID 2420282Notes

Reaction equation

HRID 2420282 reaction equation
O1CC=CC2C=CC3C(C1=2)=CC=CC=3.[O:15]1[CH:17]2[C:18]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:19]=3[O:20][CH2:21][CH:16]12.[CH:30]([NH2:33])([CH3:32])[CH3:31]>C(O)C>[CH:30]([NH:33][C@H:17]1[C@H:16]([OH:15])[CH2:21][O:20][C:19]2[C:22]3[C:27]([CH:28]=[CH:29][C:18]1=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 123289782H-Naphtho(1,2-b)pyranHCID 20311440HCID 20311440, compound

Product 1

HCID 70620286TRANS-4-ISOPROPYLAMINO-3,4-DIHYDRO-2H-NAPHTHO[1,2-b]PYRAN-3-OL

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2H-Naphtho[1,2-b]pyran (4.00 g., prepared via cyclisation of 1-naphthyl propargyl ether in diethylaniline at 210°) was converted, via the same route as that described in Example 3, to 3,4-epoxy-3,4-dihydro-2H-naphtho[1,2-b]pyran (1.44 g.) m.p. 96°-99°. This epoxide (1.40g.) was treated with isopropylamine (1.00g., an excess) in refluxing ethanol (100 ml.) for 24 hours. Work-up as described in Example 4 yielded trans-4-isopropylamino-3,4-dihydro-2H-naphtho[1,2-b]pyran-3-ol D-(+)-hydrogen tartrate hydrate (0.30 g.) m.p. 108° - 110°.

Sources & evidence

ORD record
ord-5c675c65982248db8ef5e66e654ceec1
Source dataset
uspto-grants-1978_08
Patent number
US04110347

Reaction notes

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