3-(Bromomethyl)benzoic acid → (cis)-3-(4-(3,4-Dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydro-1H-phthalazin-2-ylmethyl)benzoic acid

HRID 1871410Notes

Reaction equation

HRID 1871410 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C@H:20]3[C@H:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)[C:14](=[O:21])[NH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Br[CH2:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([OH:29])=[O:28].COC1C=C(C2[C@H]3[C@H](CCCC3)C(=O)N(CC3C=CC(C(O)=O)=CC=3)N=2)C=CC=1OC>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C@H:20]3[C@H:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)[C:14](=[O:21])[N:13]([CH2:23][C:24]3[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=3)[C:27]([OH:29])=[O:28])[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 3

HCID 2456503-(Bromomethyl)benzoic acidHCID 10913208(cis)-4-(3,4-Dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-oneHCID 86755615(cis)-4-(4-(3,4-Dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydro-1H-phthalazin-2-ylmethyl)-benzoic acid

Product 1

HCID 9866910(cis)-3-(4-(3,4-Dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydro-1H-phthalazin-2-ylmethyl)benzoic acid

Procedure

Prepared from compound 1 and 3-bromomethylbenzoic acid as described for compound 83. Purified by chromatography (ethyl acetate). Crystallized from diethyl ether. M.p. 133°-136° C.

Workup

  1. customPurified by chromatography (ethyl acetate)
  2. customCrystallized from diethyl ether

Sources & evidence

ORD record
ord-d078ea558e744fc3ade6f57c1302c972
Source dataset
uspto-grants-2000_08
Patent number
US06103718

Reaction notes

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