3,4-Dichlorobenzyl chloride → HCID 20495823, compound

HRID 1413800Notes

Reaction equation

HRID 1413800 reaction equation
ClC1C=C2C(=CC=1)C(=O)NN=C2C(OC)=O.ClC1C=C(C=CC=1Cl)CCl.ClC1C=C(C=CC=1Cl)CN1N=C(C(O)=O)C2C(=CC(F)=CC=2)C1=O.[Cl:51][C:52]1[CH:53]=[C:54]([CH:72]=[CH:73][C:74]=1[Cl:75])[CH2:55][N:56]1[N:65]=[C:64]([C:66]([OH:68])=[O:67])[C:63]2[C:58](=[CH:59][C:60](Cl)=[C:61]([Cl:69])[CH:62]=2)[C:57]1=[O:71]>>[Cl:51][C:52]1[CH:53]=[C:54]([CH:72]=[CH:73][C:74]=1[Cl:75])[CH2:55][N:56]1[N:65]=[C:64]([C:66]([OH:68])=[O:67])[C:63]2[C:58](=[CH:59][CH:60]=[C:61]([Cl:69])[CH:62]=2)[C:57]1=[O:71]

Participants

5

Reactant 4

HCID 76093,4-Dichlorobenzyl chlorideHCID 20495792HCID 20495792, compoundHCID 20495834HCID 20495834, compoundHCID 20495836HCID 20495836, compound

Product 1

HCID 20495823HCID 20495823, compound

Procedure

This ester was then reacted with 3,4-dichlorobenzyl chloride in an analogous manner to that described in part (i) and (ii) above. There was then obtained methyl 2-(3,4-dichlorobenzyl)-6-chloro-1,2-dihydro-1-oxophthalazin-4-ylcarboxylate, m.p. 168°-170° C. (recrystallised from toluene) in 45% yield. This ester was then hydrolysed as described in part (i) above to give 2-(3,4-dichlorobenzyl)-6-chloro-1,2-dihydro-1-oxophthalazin-4-ylcarboxylic acid, m.p. 222°-223° C. (recrystallised from ethanol) in 60% yield.

Workup

  1. customobtained methyl 2-(3,4-dichlorobenzyl)-6-chloro-1,2-dihydro-1-oxophthalazin-4-ylcarboxylate, m.p. 168°-170° C. (recrystallised from toluene) in 45% yield
  2. customto give
  3. custom2-(3,4-dichlorobenzyl)-6-chloro-1,2-dihydro-1-oxophthalazin-4-ylcarboxylic acid, m.p. 222°-223° C. (recrystallised from ethanol) in 60% yield

Sources & evidence

ORD record
ord-063c6f3810c14492b5c736b9ab181c0f
Source dataset
uspto-grants-1981_02
Patent number
US04251528

Reaction notes

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