Allyl bromide → 3-Allyloxy-6-chloro-5,9-diaza-benzo[c]fluoren-7-one

HRID 1840418Notes

Reaction equation

HRID 1840418 reaction equation
[Cl:1][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:4]=2[N:3]=1.[CH2:21](Br)[CH:22]=[CH2:23]>>[CH2:23]([O:20][C:18]1[CH:17]=[CH:16][C:5]2[C:6]3[C:7]4[CH:8]=[CH:9][N:10]=[CH:11][C:12]=4[C:13](=[O:15])[C:14]=3[C:2]([Cl:1])=[N:3][C:4]=2[CH:19]=1)[CH:22]=[CH2:21]

Participants

3

Reactant 2

HCID 7841Allyl bromideHCID 1357900736-Chloro-3-hydroxy-5,9-diaza-benzo[c]fluoren-7-one

Product 1

HCID 234480363-Allyloxy-6-chloro-5,9-diaza-benzo[c]fluoren-7-one

Procedure

This compound was prepared from 6-chloro-3-hydroxy-5,9-diaza-benzo[c]fluoren-7-one (Example 34a) and allyl bromide in a similar manner to Example 34b. The desired product was obtained as a yellow powder. ESI−MS: m/z 323 (MH+); 1H-NMR (CDCl3): δ4.75 (2H, dt, J=5 Hz, 1 Hz), 5.41 (1H, dq, J=11 Hz, 1 Hz), 5.52 (1H, dq, J=17 Hz, 1 Hz), 6.12 (1H, ddt, J=17 Hz, 11 Hz, 5 Hz), 7.43 (1H, dd, J=8 Hz, 1.5 Hz), 7.45 (1H, s), 8.01 (1H, dd, J=5 Hz, 1 Hz), 8.36 (1H, dd, J=8 Hz, 1.5 Hz), 8.96 (1H, d, J=5 Hz), 9.04 (1H, d, J=1 Hz).

Sources & evidence

ORD record
ord-0ce36b803317429abb75221fb27caf3a
Source dataset
uspto-grants-2004_01
Patent number
US06680326B2

Reaction notes

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