Phthalic Anhydride → HCID 21702120, compound

HRID 1596607Notes

Reaction equation

HRID 1596607 reaction equation
[C:1]1(=O)O[C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C[CH:13]([NH2:20])[C:14]1[CH:19]=CC=CC=1.[C:21](Cl)(=O)[CH2:22][CH3:23].NN.O.[C:29]([S-:31])#[N:30].[K+].BrBr.C[CH2:36][N:37](CC)CC>[Pd].CC(O)=O.CCO.C(Cl)Cl.CO.C1(C)C=CC=CC=1>[NH2:37][CH:36]1[CH2:4][C:3]2[C:2](=[CH:10][C:9]3[S:31][C:29]([N:20]([CH2:13][CH2:14][CH3:19])[CH2:21][CH2:22][CH3:23])=[N:30][C:8]=3[CH:7]=2)[CH2:1]1

Participants

14

Reactant 7

HCID 6811Phthalic Anhydride2×HCID 74081-PhenethylamineHCID 8471Triethylamine2×HCID 24408BromineHCID 24654Hydrazine hydrate (1:1)HCID 62324Propionyl chlorideHCID 516872Potassium thiocyanate

Product 1

HCID 21702120HCID 21702120, compound

Reagents, catalysts & solvents 6

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×HCID 702EthanolSolventHCID 887MethanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

Reagents: (a) α-methyl-benzylamine, cat. p-TosOH, toluene, Δ; (b) H2, Pd/C 10%, MeOH; (c) Phtalic anhydride, HOAc, Δ; (d) propionylchloride, Et3N, CH2Cl2; (e) propionylchloride, Et3N, CH2Cl2; (f) H2NNH2.H2O, EtOH, Δ; (g) KSCN, Br2, HOAc, r.t.; (h) separation of diastereomers and possible regioisomers; (i) LiAlH4, Et2O, r.t.; (j) HCO2NH4, Pd/C 10%, MeOH, A; (k) propionylchloride, Et3N, CH2Cl2; (l) BH3in THF, Et2O, Δ.

Workup

  1. custom(h) separation of diastereomers and possible regioisomers
  2. custom(i) LiAlH4, Et2O, r.t.

Sources & evidence

ORD record
ord-0859a801f2f8418c99f3ab0370c8147d
Source dataset
uspto-grants-2001_09
Patent number
US06291494B1

Reaction notes

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