5-Nitrosalicylaldehyde → Phthalic Anhydride

HRID 2351366Notes

Reaction equation

HRID 2351366 reaction equation
[N+](C1C=C(C=O)C(O)=CC=1)([O-])=[O:2].C(C[C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19])#N.C(COC1C=CC=CC=1C([O-])=O)#N.B#B>O1CCCC1>[C:21]1(=[O:2])[O:20][C:18](=[O:19])[C:17]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:16]12

Participants

6

Reactant 4

HCID 668085-NitrosalicylaldehydeHCID 588805Methyl 2-(cyanomethyl)benzoateHCID 6328200DiboronHCID 19846253HCID 19846253, compound

Product 1

HCID 6811Phthalic Anhydride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The intermediates for reacting with 5-nitrosalicylaldehyde to prepare compounds wherein --Y-- contains an ethylbenzyl or ethoxybenzyl group were prepared by the reduction of the appropriate methyl cyanomethylbenzoate or cyanomethoxybenzoate with diborane in tetrahydrofuran solution, followed by the reaction of the amino compound thus obtained with phthalic anhydride at 100° C. and then with phosphorus tribromide also at 100° C. The various intermediates which were characterised have melting points as follows: 4-(2-aminoethyl)benzyl alcohol hydrochloride m.p. 160°-162° C. 3-(2-aminoethyl)benzyl alcohol hydrochloride m.p. 115°-118° C. 2-(2-aminoethyl)benzyl alcohol hydrochloride m.p. 103°-104° C. 4-(2-aminoethoxy)benzyl alcohol m.p. 92°-94° C. 3-(2-aminoethoxy)benzyl alcohol hydrochloride m.p. 143°-145° C. 4-(2-phthalimidoethyl)benzyl bromide 158°-161° C. 3-(2-phthalimidoethyl)benzyl bromide 93°-94° C. 2-(2-phthalimidoethyl)benzyl bromide 140°-141° C. 3-(2-phthalimidoethoxy)benzyl bromide 116°-117° C. 4-(2-phthalimidoethoxy)benzyl chloride 109°-112° C. (prepared by reacting with mesyl chloride and triethylamine in place of phosphorus tribromide).

Workup

  1. customto prepare compounds wherein

Sources & evidence

ORD record
ord-4a6dcdc2a80c4ddca0c15e99be838659
Source dataset
uspto-grants-1989_10
Patent number
US04873254

Reaction notes

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