4-(Chloromethyl)benzoic acid → (cis)-4-(4-(3,4-Diethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydro-1H-phthalazin-2-yl-methyl)benzoic acid

HRID 1871407Notes

Reaction equation

HRID 1871407 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[C@H:22]3[C@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]3)[C:16](=[O:23])[NH:15][N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].Cl[CH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=1.COC1C=C(C2[C@H]3[C@H](CCCC3)C(=O)N(CC3C=CC(C(O)=O)=CC=3)N=2)C=CC=1OC>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[C@H:22]3[C@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]3)[C:16](=[O:23])[N:15]([CH2:25][C:26]3[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 3

HCID 742344-(Chloromethyl)benzoic acidHCID 70002320(cis)-4-(3,4-Diethoxyphenyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-onHCID 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 86755616(cis)-4-(4-(3,4-Diethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydro-1H-phthalazin-2-yl-methyl)benzoic acid

Procedure

Prepared from compound 7 and 4-chloromethylbenzoic acid as described for compound 83. Purified by chromatography (dichloromethane). Crystallized from diethyl ether. M.p. 152°-154° C.

Workup

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

Sources & evidence

ORD record
ord-22b4b89fece345fa8460d5213a2d2755
Source dataset
uspto-grants-2000_08
Patent number
US06103718

Reaction notes

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